50 Best Boston Apartments on Holiday Lettings - Condos

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950 Vacation rentals

(1) Good 

    6

    Vacation apartment in Boston

    Massachusetts / Boston

    1 4 min stay varies

    • 1 bedroom
    • sleeps 4
    • min stay varies
    • Air conditioning
    Large, bright apartment located steps from Coolidge Corner. 1 bed/1 bath. Fully equipped kitchen with dishwasher. There is also a gym and laundry located in the building. Across the street from a T stop and walking distance to the heart of Coolidge Corner.

    Pricing unknown

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    Pricing unknown

      35

      Vacation studio with shared pool in Boston

      Massachusetts / Boston

      Studio 2 3 nights min

      • Studio
      • sleeps 2
      • 3 nights min
      • Swimming pool
      • Child friendly
      • Air conditioning
      Located just minutes from downtown and the Back Bay, the South End has become one of Boston's most popular neighborhoods. A family-friendly and diverse neighborhood within range of the Prudential Center and the Back Bay skyline. Victorian row houses and well-maintained

      from $344 / night

      $2,405 / week

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      from $344 / night

        35

        Vacation apartment with shared pool in Boston

        Massachusetts / Boston

        1 4 3 nights min

        • 1 bedroom
        • sleeps 4
        • 3 nights min
        • Swimming pool
        • Child friendly
        • Air conditioning
        Located just minutes from downtown and the Back Bay, the South End has become one of Boston's most popular neighborhoods. A family-friendly and diverse neighborhood within range of the Prudential Center and the Back Bay skyline. Victorian row houses and well-maintained

        from $401 / night

        $2,806 / week

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        from $401 / night

          39

          Vacation apartment rental

          Massachusetts / Boston

          2 5 3 nights min

          • 2 bedrooms
          • sleeps 5
          • 3 nights min
          • Child friendly
          • Air conditioning
          Although Back Bay is centrally located, the area is strewn with countless public parks and retreats for business travellers. Lederman Park, to the west, and the Christopher Columbus Park to the east, are two of Massachusetts most peaceful parks. Copley Place shopping ce

          from $573 / night

          $4,008 / week

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          from $573 / night

            4

            Vacation apartment in Boston

            Massachusetts / Boston

            1 4 1 night min

            • 1 bedroom
            • sleeps 4
            • 1 night min
            • Child friendly
            Great one bedroom apartment with lots of living space and large full bathroom. Complete kitchen including dishwasher and microwave. Free internet and cable access. 24 doorman and paid parking available in lower garage. Many nearby restaurants, bars and a Walgreens. Also

            from $1,289 / night

            $6,441 / week

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            from $1,289 / night

              4

              Vacation home in Boston

              Massachusetts / Boston

              1 3 1 night min

              • 1 bedroom
              • sleeps 3
              • 1 night min
              • Child friendly
              • Air conditioning
              Beautiful one bedroom penthouse apartment with small balcony overlooking Boston harbor and airport. Walk-able to all major tourist destinations including Fanueil Hall and Quincy market. Many nearby restaurants and bars. Right next to the blue and orange line T stops. Do

              from $1,487 / night

              $7,436 / week

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              from $1,487 / night

                27

                Vacation apartment in Boston

                Massachusetts / Boston

                2 5 min stay varies

                • 2 bedrooms
                • sleeps 5
                • min stay varies
                • Child friendly
                Dazzling city views await during your stay at this stunning, bright and open 5th-floor corner Boston loft apartment near vibrant Chinatown. This beautiful 2-bedroom, 1-bathroom furnished loft apartment in Boston comes complete with a spacious open floor plan, 11-foot c

                from $132 / night

                $922 / week

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                avg. 2 hours 31 minutes

                from $132 / night

                (2) Excellent 

                  19

                  Vacation apartment in Boston

                  Massachusetts / Boston

                  2 7 1 night min

                  • 2 bedrooms
                  • sleeps 7
                  • 1 night min
                  • Child friendly
                  • Car not necessary
                  • Air conditioning
                  Private 3Bd Condo Near Airport Train Station Boston only minutes to downtown This condo is on two levels. Level 1 has two bedrooms and one full bath (WC, vanity and bathtub), the 3rd bedroom is on basement level with an additional bathroom (WC, vanity and shower). Our

                  from $430 / night

                  $2,691 - $3,035 / week

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                  avg. 1 hour 51 minutes

                  from $430 / night

                  (1) Excellent 

                    22

                    Vacation apartment in Boston

                    Massachusetts / Boston

                    2 4 3 nights min

                    • 2 bedrooms
                    • sleeps 4
                    • 3 nights min
                    • Suitable for children age 5+
                    • Car not necessary
                    • Air conditioning
                    Our Historic Beacon Hill, Two bedroom, Queen size beds, duplex Condo, is comfortable and well located. An ideal central location for exploring or working in the heart of Boston at: 27 Ridgeway Lane, Beacon Hill, Boston, 02114. Great Restaurants nearby. Access to ALL p

                    from $350 / night

                    $2,445 / week

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                    Responds fast!
                    avg. 2 hours 18 minutes

                    from $350 / night

                    (3) Very Good 

                      35

                      Vacation apartment rental

                      Massachusetts / Boston

                      2 5 min stay varies

                      • 2 bedrooms
                      • sleeps 5
                      • min stay varies
                      • Child friendly
                      • Air conditioning
                      Offering the best of old-world Boston and the newest 21-century conveniences, this charming Garrison Street two-bedroom might take you back in time. But the modern interior, featuring a full kitchen and fast WiFi, will bring you right back to today. The spacious layout

                      from $115 / night

                      $802 / week

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                      from $115 / night

                      (17) Very Good 

                        24

                        Apartment rental in Boston

                        Massachusetts / Boston

                        2 6 3 nights min

                        • 2 bedrooms
                        • sleeps 6
                        • 3 nights min
                        • Child friendly
                        • Air conditioning
                        • Pet friendly
                        Find Boston Vacation Rentals on FlipKey Find Boston Vacation Rentals on FlipKey Modern apartment in a JP 2 family. Enjoy our extensive collection of fresh local art. This is not your standard run of the mill rental. Collection will occasionally rotate. Currently showing

                        from $286 / night

                        $1,890 - $2,691 / week

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                        avg. 3 hours 25 minutes

                        from $286 / night

                        (53) Excellent 

                        Certificate of Excellence

                          14

                          Vacation condo in Boston

                          Massachusetts / Boston

                          1 2 28 nights min

                          • 1 bedroom
                          • sleeps 2
                          • 28 nights min
                          • Car not necessary
                          • Air conditioning
                          This fully furnished apartment has a one month (31 night) minimum rental period. We've been renting high-quality furnished accommodations for over 8 years, exclusively in the Beacon Hill neighborhood. "the Nest" apartment location is stellar, just 3 minutes walking dis

                          Certificate of Excellence

                          from $275 / night

                          $1,603 / week

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                          Responds fast!
                          avg. 2 hours 55 minutes

                          from $275 / night

                          (22) Excellent 

                          Certificate of Excellence

                            30

                            Apartment rental in Boston

                            Massachusetts / Boston

                            2 4 3 nights min

                            • 2 bedrooms
                            • sleeps 4
                            • 3 nights min
                            • Child friendly
                            • Car not necessary
                            • Air conditioning
                            Brand new luxury apt is 1350 square feet that is over-looking the Boston Harbor. Spectacular views of the skylines of Boston. Watch the boats go by or relax on your oversized private deck. The deck features a Weber gas grill and a beautiful white table with four Adiro

                            Certificate of Excellence

                            from $401 / night

                            $2,405 / week

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                            avg. 2 hours 50 minutes

                            from $401 / night

                            (2) Very Good 

                              60

                              Home rental in Boston with shared pool

                              Massachusetts / Boston

                              1 4 1 night min

                              • 1 bedroom
                              • sleeps 4
                              • 1 night min
                              • Swimming pool
                              • Child friendly
                              • Car not necessary
                              Enjoy a top-notch location in downtown Boston at this modern condo. With shops, restaurants, and historic sights all around, plus updated amenities, a great balcony, and a community pool, you'll have everything you need. Located on the 30th floor of the Longfellow P

                              from $277 / night

                              $1,940 / week

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                              avg. 3 hours 7 minutes

                              from $277 / night

                              (2) Excellent 

                                8

                                Vacation condo in Boston

                                Massachusetts / Boston

                                2 6 2 nights min

                                • 2 bedrooms
                                • sleeps 6
                                • 2 nights min
                                • Beach/lakeside relaxation
                                • Air conditioning
                                Ideal location in the South Boston neighborhood, easily accessible by public transportation. Only 10 minute cab ride to/from Logan Airport. Only 10 minute walk to Convention Center!! Short walk to Downtown/Financial District, Fort Point, Seaport District and other area

                                from $344 / night

                                $2,290 / week

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                                Responds fast!
                                avg. 40 minutes

                                from $344 / night

                                  54

                                  Vacation home in Boston

                                  Massachusetts / Boston

                                  1 4 1 night min

                                  • 1 bedroom
                                  • sleeps 4
                                  • 1 night min
                                  • Swimming pool
                                  • Child friendly
                                  • Car not necessary
                                  Stay in this convenient condo in the heart of downtown Boston - complete with updated amenities, plenty of space, and access to a shared pool. Plus, you'll have a private balcony and beautiful city views for the ultimate urban retreat. Located in the West End area o

                                  from $272 / night

                                  $1,900 / week

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                                  avg. 3 hours 7 minutes

                                  from $272 / night

                                  (1) Excellent 

                                    35

                                    Vacation apartment rental

                                    Massachusetts / Boston

                                    2 5 min stay varies

                                    • 2 bedrooms
                                    • sleeps 5
                                    • min stay varies
                                    • Child friendly
                                    • Air conditioning
                                    Offering the best of old-world Boston and the newest 21-century conveniences, this charming Garrison Street two-bedroom might take you back in time. But the modern interior, featuring a full kitchen and fast WiFi, will bring you right back to today. The spacious layout

                                    from $115 / night

                                    $802 / week

                                    Book View

                                    from $115 / night

                                    (4) Very Good 

                                      35

                                      Vacation apartment accommodation

                                      Massachusetts / Boston

                                      2 5 min stay varies

                                      • 2 bedrooms
                                      • sleeps 5
                                      • min stay varies
                                      • Child friendly
                                      • Air conditioning
                                      Offering the best of old-world Boston and the newest 21-century conveniences, this charming Garrison Street two-bedroom might take you back in time. But the modern interior, featuring a full kitchen and fast WiFi, will bring you right back to today. The spacious layout

                                      from $115 / night

                                      $802 / week

                                      Book View

                                      from $115 / night

                                      (1) Excellent 

                                        13

                                        Vacation apartment in Boston

                                        Massachusetts / Boston

                                        1 3 4 nights min

                                        • 1 bedroom
                                        • sleeps 3
                                        • 4 nights min
                                        • Suitable for children age 5+
                                        • Car not necessary
                                        • Air conditioning
                                        Bright, sunny, top floor 1 bedroom located on the most beautiful street in Boston's Back Bay. If you are looking for a quite, bright, homey place you will love this one bedroom apartment. Located on the top floor (4th) of a walk up, in a traditional brownstone buildin

                                        from $229 / night

                                        $1,374 / week

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                                        from $229 / night

                                          32

                                          Vacation apartment rental

                                          Massachusetts / Boston

                                          1 4 1 night min

                                          • 1 bedroom
                                          • sleeps 4
                                          • 1 night min
                                          • Child friendly
                                          This lovely apartment features hardwood floors, fully equipped kitchen and a spacious bedroom. Located in Theater District, just steps to Boston Common and the Back Bay. This apartment features an open space living area, a spacious kitchen, hardwood floors, walking dis

                                          from $189 / night

                                          $1,323 / week

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                                          avg. 3 hours 58 minutes

                                          from $189 / night

                                          (1) Excellent 

                                            17

                                            Vacation apartment in Boston

                                            Massachusetts / Boston

                                            1 1 30 nights min

                                            • 1 bedroom
                                            • sleeps 1
                                            • 30 nights min
                                            • Air conditioning
                                            1 Private room, shared kitchen & bathroom with other student/professional. Less than 3 mins walk to Red line train, food, market shops near by, 15 mins train ride to Downtown Boston, 20 min to MGH, 30 min to Longwood hospital Beth Israel, Downtown Financial District.

                                            from $35 / night

                                            $241 / week

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                                            avg. 3 hours 10 minutes

                                            from $35 / night

                                              9

                                              Vacation condo in Boston

                                              Massachusetts / Boston

                                              1 2 1 night min

                                              • 1 bedroom
                                              • sleeps 2
                                              • 1 night min
                                              • Air conditioning
                                              • Pet friendly
                                              • Private garden
                                              Located in the Sumner Hill area of Jamaica Plain. Close to Centre Street shops and restaurants as well as pond and Arboretum. Walkable to public transportation - 6 minutes to South end or Back Bay. This is a comfortable living space with full kitchen for dining in. Yo

                                              from $172 / night

                                              $1,088 / week

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                                              avg. 3 hours 21 minutes

                                              from $172 / night

                                                13

                                                Vacation apartment rental

                                                Massachusetts / Boston

                                                1 1 30 nights min

                                                • 1 bedroom
                                                • sleeps 1
                                                • 30 nights min
                                                • Car not necessary
                                                • Air conditioning
                                                • Private garden
                                                1 Private room, shared kitchen & bathroom with other student/professional. Less than 3 mins walk to Red line train, food, market shops near by, 15 mins train ride to Downtown Boston, 20 min to MGH, 30 min to Longwood hospital Beth Israel, Downtown Financial District.

                                                from $52 / night

                                                $361 / week

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                                                avg. 3 hours 10 minutes

                                                from $52 / night

                                                  21

                                                  Apartment rental in Boston

                                                  Massachusetts / Boston

                                                  3 6 min stay varies

                                                  • 3 bedrooms
                                                  • sleeps 6
                                                  • min stay varies
                                                  • Child friendly
                                                  • Air conditioning
                                                  Convenience and comfort all in one apartment. Stay at our newly listed 3 bedroom and 2 bathroom apartment in the heart of North End's Little Italy. Dine at famous restaurants like Neptune's Oyster, Pizzeria Regina, Giacomo's Restaurant, Mike's Pastry, and more. Be steps

                                                  from $171 / night

                                                  $1,074 / week

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                                                  Responds fast!
                                                  avg. 1 hour 15 minutes

                                                  from $171 / night

                                                    61

                                                    Vacation apartment in Boston

                                                    Massachusetts / Boston

                                                    2 6 1 night min

                                                    • 2 bedrooms
                                                    • sleeps 6
                                                    • 1 night min
                                                    • Child friendly
                                                    • Car not necessary
                                                    • Air conditioning
                                                    Experience the vibrant, contemporary style of South Boston at this two-bedroom condo, where you'll enjoy building amenities that include a gym, a game room, and a grilling patio, as well as wonderful access to the Seaport District, the T Red Line, and Logan Internationa

                                                    from $329 / night

                                                    $2,301 / week

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                                                    avg. 3 hours 12 minutes

                                                    from $329 / night

                                                    (1) Excellent 

                                                      22

                                                      Boston Vacation home accommodation

                                                      Massachusetts / Boston

                                                      1 3 2 nights min

                                                      • 1 bedroom
                                                      • sleeps 3
                                                      • 2 nights min
                                                      • Child friendly
                                                      • Car not necessary
                                                      Your next room. Renovated House located on the 3rd fl with 5 bedrooms. King size bed in a private room . Patio/backyard for you to relax, cook and enjoy. 2 bathroom and a full kitchen with coffee maker, toaster, blender and all cookware. We provide free linens, towels.

                                                      from $127 / night

                                                      $890 / week

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                                                      from $127 / night

                                                        17

                                                        Boston Vacation apartment rental

                                                        Massachusetts / Boston

                                                        1 3 min stay varies

                                                        • 1 bedroom
                                                        • sleeps 3
                                                        • min stay varies
                                                        • Child friendly
                                                        Back Bay is a shopping and dining destination. Well-heeled locals frequent designer boutiques, fashion chains, art galleries and patio cafes set in elegant brick townhouses. Expansive Copley Square is flanked by 1800s landmarks Trinity Church and the Boston Public Libra

                                                        from $166 / night

                                                        $1,143 / week

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                                                        avg. 2 hours 27 minutes

                                                        from $166 / night

                                                        (4) Excellent 

                                                          26

                                                          Vacation apartment in Boston

                                                          Massachusetts / Boston

                                                          4 8 3 nights min

                                                          • 4 bedrooms
                                                          • sleeps 8
                                                          • 3 nights min
                                                          • Ask about children
                                                          This perfectly situated 4 bedroom apartment & 2 full baths was just completely renovated in 2014. Each bedroom features queen size beds. It has brand new full kitchen with granite countertops and new cabinets. Open living room with decorative fireplace. Hardwood floor t

                                                          from $430 / night

                                                          $2,977 / week

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                                                          from $430 / night

                                                            9

                                                            Vacation condo in Boston

                                                            Massachusetts / Boston

                                                            2 6 2 nights min

                                                            • 2 bedrooms
                                                            • sleeps 6
                                                            • 2 nights min
                                                            • Car not necessary
                                                            • Air conditioning
                                                            • Pet friendly
                                                            Newly renovated two bedroom apartment available close to Seaport, two blocks from convention center and one subway stop to South Station. Open deck, short walk to grocery store and restaurants, very close to airport and few blocks from major subway line. Minutes to Down

                                                            from $344 / night

                                                            $2,290 - $2,691 / week

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                                                            Responds fast!
                                                            avg. 3 hours 54 minutes

                                                            from $344 / night

                                                            (2) Excellent 

                                                              17

                                                              Vacation apartment in Boston

                                                              Massachusetts / Boston

                                                              2 5 1 night min

                                                              • 2 bedrooms
                                                              • sleeps 5
                                                              • 1 night min
                                                              • Child friendly
                                                              Our condo/apartment is a 2 minute walk to great restaurants, convenience stores, the Blue Line airport T-subway station, only two stations away from downtown Boston. There is a Free shuttle bus between the Airport T-station and the airport terminals. You will not need a

                                                              from $286 / night

                                                              $2,061 / week

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                                                              Responds fast!
                                                              avg. 1 hour 51 minutes

                                                              from $286 / night

                                                              (13) Excellent 

                                                                59

                                                                Vacation apartment in Boston

                                                                Massachusetts / Boston

                                                                1 2 2 nights min

                                                                • 1 bedroom
                                                                • sleeps 2
                                                                • 2 nights min
                                                                • Air conditioning
                                                                Comfortable, elegant, and romantic! Three-room luxury art suite with authentic European furnishings. In beautifully restored, award-winning historic townhouse located in Boston's oldest neighborhood of Charlestown! Lovely, walkable district near Freedom Trail, Bunker H

                                                                from $339 / night

                                                                $1,718 / week

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                                                                avg. 3 hours 12 minutes

                                                                from $339 / night

                                                                  18

                                                                  Vacation condo in Boston

                                                                  Massachusetts / Boston

                                                                  1 3 3 nights min

                                                                  • 1 bedroom
                                                                  • sleeps 3
                                                                  • 3 nights min
                                                                  Our North End vacation home was designed to make us feel like we are staying in a 5 star luxury hotel... it will make you feel that way too. Located in Boston's historic North End and just steps away from the Waterfront, Rose Kennedy Greenway, Freedom Trail, Paul Rever

                                                                  from $287 / night

                                                                  $1,890 / week

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                                                                  avg. 2 hours 26 minutes

                                                                  from $287 / night

                                                                    29

                                                                    Vacation apartment in Boston

                                                                    Massachusetts / Boston

                                                                    1 4 1 night min

                                                                    • 1 bedroom
                                                                    • sleeps 4
                                                                    • 1 night min
                                                                    • Child friendly
                                                                    This apartment features an open-space , living area, a spacious kitchen, hardwood floors. Located in the Theater District, walking distance to Boston Common and the Back Bay. All bookings instantly confirmed. Every call or message answered in minutes. The apartment is

                                                                    from $189 / night

                                                                    $1,323 / week

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                                                                    avg. 3 hours 58 minutes

                                                                    from $189 / night

                                                                      15

                                                                      Boston Vacation apartment rental

                                                                      Massachusetts / Boston

                                                                      1 3 7 nights min

                                                                      • 1 bedroom
                                                                      • sleeps 3
                                                                      • 7 nights min
                                                                      • Child friendly
                                                                      • Air conditioning
                                                                      • Pet friendly
                                                                      Seven30 East Broadway offers beautiful new condos in South Boston. What seems like a typical residential building with simple windows, takes luxury up a notch. Inside this nondescript building, you may just find the apartment of your dreams. Very Spacious floor plans, F

                                                                      from $297 / night

                                                                      $2,076 / week

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                                                                      from $297 / night

                                                                      (78) Very Good 

                                                                        39

                                                                        Boston Vacation apartment rental

                                                                        Massachusetts / Boston

                                                                        2 5 min stay varies

                                                                        • 2 bedrooms
                                                                        • sleeps 5
                                                                        • min stay varies
                                                                        • Child friendly
                                                                        • Air conditioning
                                                                        This gorgeous West End condo makes a wonderful Boston home base, as long as you enjoy rooftop terraces, contemporary decor, and all the comforts of home. This fully-equipped two-bedroom provides modern amenities like fast WiFi, in-unit laundry, and a kitchen with fancy

                                                                        from $155 / night

                                                                        $1,082 / week

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                                                                        from $155 / night

                                                                          41

                                                                          Vacation apartment in Boston

                                                                          Massachusetts / Boston

                                                                          2 6 min stay varies

                                                                          • 2 bedrooms
                                                                          • sleeps 6
                                                                          • min stay varies
                                                                          • Child friendly
                                                                          • Air conditioning
                                                                          • Pet friendly
                                                                          "South Boston, or "Southie," is an evolving residential neighborhood with a strong Irish-American heritage. Old-school diners and taverns mingle with pizzerias and gastropubs. Marking a Revolutionary War site, the Dorchester Heights monument offers sweeping Boston Harbo

                                                                          from $401 / night

                                                                          $2,806 / week

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                                                                          avg. 3 hours 55 minutes

                                                                          from $401 / night

                                                                            41

                                                                            Vacation apartment in Boston

                                                                            Massachusetts / Boston

                                                                            1 5 2 nights min

                                                                            • 1 bedroom
                                                                            • sleeps 5
                                                                            • 2 nights min
                                                                            • Child friendly
                                                                            • Pet friendly
                                                                            A beautiful high ceiling large one bedroom with an old graceful charm. Sleeps 4-5 with one king and one twin size bed in the large bedroom and a sleeper sofa and a day bed in dining. The apartment is located in the best location on the 2nd floor, sunny, facing Hanover s

                                                                            from $171 / night

                                                                            $1,195 / week

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                                                                            from $171 / night

                                                                            (48) Very Good 

                                                                              36

                                                                              Vacation apartment rental

                                                                              Massachusetts / Boston

                                                                              3 7 min stay varies

                                                                              • 3 bedrooms
                                                                              • sleeps 7
                                                                              • min stay varies
                                                                              • Swimming pool
                                                                              • Child friendly
                                                                              • Air conditioning
                                                                              This upscale three-bedroom apartment is the ultimate Beantown abode for business travelers, vacationers, and seafood aficionados who want comfort and convenience. Featuring a fully-equipped kitchen, in-unit laundry, and public transportation pretty much on your doorstep

                                                                              from $172 / night

                                                                              $1,203 / week

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                                                                              from $172 / night

                                                                                11

                                                                                Boston Vacation apartment rental

                                                                                Massachusetts / Boston

                                                                                2 4 min stay varies

                                                                                • 2 bedrooms
                                                                                • sleeps 4
                                                                                • min stay varies
                                                                                • Air conditioning
                                                                                Open layout two bedroom apartment in Boston's Little Italy makes for the ideal family getaway, business trip, or reunion of friends. With plenty of natural light, breathtaking views, and bright decor, you will be located among all the best that Boston has to offer from

                                                                                from $114 / night

                                                                                $714 / week

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                                                                                avg. 1 hour 15 minutes

                                                                                from $114 / night

                                                                                  16

                                                                                  Boston Vacation home rental

                                                                                  Massachusetts / Boston

                                                                                  1 3 2 nights min

                                                                                  • 1 bedroom
                                                                                  • sleeps 3
                                                                                  • 2 nights min
                                                                                  • Child friendly
                                                                                  • Air conditioning
                                                                                  Private Bedroom Suite on Jamaica Plain triple Decker. Very comfortable room in very spacious, clean house. Best room/suite in Boston under $200. The space This is a multi-level, grand house with a lot of space and very close proximity to the inner city. You will be st

                                                                                  from $178 / night

                                                                                  $1,243 / week

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                                                                                  avg. 3 hours 27 minutes

                                                                                  from $178 / night