50 Best Boston Apartments on Holiday Lettings - Condos

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858 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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      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 $1,285 / night

      $6,425 / week

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      from $1,285 / 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 $1,440 / night

        $7,199 / week

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        from $1,440 / 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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          avg. 2 hours 18 minutes

          from $350 / 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 34 minutes

            from $132 / night

              23

              Vacation apartment in Boston

              Massachusetts / Boston

              4 12 min stay varies

              • 4 bedrooms
              • sleeps 12
              • min stay varies
              • Nearest beach 6 mi
              • Child friendly
              • Car not necessary
              Completely renovated , duplex apartment in a two family house. Walls of windows, very sunny, and cheerful. There are two units in this house. Unit #2 is on the 2nd and 3rd floors of the house. Unit #2 has four large bedrooms , two and half tiled bath in total . Three

              from $516 / night

              $2,290 - $11,908 / week

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              avg. 2 hours 19 minutes

              from $516 / 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. 2 hours 22 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 46 minutes

                  from $275 / 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 $148 / night

                    $1,034 / week

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                    from $148 / night

                    (23) 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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                      Responds fast!
                      avg. 3 hours 42 minutes

                      from $401 / night

                      (5) 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 $148 / night

                        $1,034 / week

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                        from $148 / 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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                          from $344 / night

                          (3) Good 

                            39

                            Apartment rental in Boston

                            Massachusetts / Boston

                            3 8 5 nights min

                            • 3 bedrooms
                            • sleeps 8
                            • 5 nights min
                            • Nearest beach 2 mi
                            • Child friendly
                            • Car not necessary
                            This Brown Stone apartment is right in the heart of academic area of Boston Between Long Wood and Fen Way area. Two subway stations and bus terminal just 5 minutes walk away. Street parking , two hour limit during the day and free at night except snow emergency and stre

                            from $401 / night

                            $2,061 - $2,542 / week

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                            Responds fast!
                            avg. 2 hours 19 minutes

                            from $401 / 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

                              (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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                                Responds fast!
                                avg. 3 hours 23 minutes

                                from $35 / night

                                (1) Excellent 

                                  12

                                  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

                                    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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                                    from $52 / night

                                      32

                                      Vacation apartment rental

                                      Massachusetts / Boston

                                      1 4 min stay varies

                                      • 1 bedroom
                                      • sleeps 4
                                      • min stay varies
                                      • 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 14 minutes

                                      from $189 / 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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                                        avg. 3 hours 18 minutes

                                        from $171 / 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

                                          $3,035 / week

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                                          avg. 1 hour 15 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. 2 hours 32 minutes

                                            from $339 / 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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                                              avg. 3 hours 54 minutes

                                              from $344 / 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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                                                Responds fast!
                                                avg. 3 hours 21 minutes

                                                from $172 / night

                                                  43

                                                  Vacation condo in Boston

                                                  Massachusetts / Boston

                                                  2 8 6 nights min

                                                  • 2 bedrooms
                                                  • sleeps 8
                                                  • 6 nights min
                                                  • Air conditioning
                                                  Enjoy a large modern, clean 2 bedrooms / 3 beds + bathroom + full kitchen Bus stops, train stations and downtown are all walking distance. Food store across the street, Whole Foods, coffee shops, bars, restaurants, gym and pool all nearby. Historic sites are all walkin

                                                  from $228 / night

                                                  $1,488 / week

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                                                  from $228 / 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

                                                    (1) Excellent 

                                                      33

                                                      Apartment rental in Boston

                                                      Massachusetts / Boston

                                                      1 3 2 nights min

                                                      • 1 bedroom
                                                      • sleeps 3
                                                      • 2 nights min
                                                      • Car not necessary
                                                      • Air conditioning
                                                      Dressed exclusively for short term rentals 1-bedroom on the 1st floor -parlor with astonishing ceilings, new tall custom windows, new SS appliances and the best of Boston outside your door. Located ½ a block to Restaurant Row, where you’ll find some of the best dining

                                                      from $228 / night

                                                      $1,946 - $2,186 / week

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                                                      from $228 / 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

                                                          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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                                                          Responds fast!
                                                          avg. 3 hours 18 minutes

                                                          from $114 / 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 $116 / night

                                                            $810 / week

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                                                            from $116 / 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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                                                              Responds fast!
                                                              avg. 2 hours 4 minutes

                                                              from $287 / 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

                                                                  57

                                                                  Boston Vacation home rental

                                                                  Massachusetts / Boston

                                                                  10 20 min stay varies

                                                                  • 10 bedrooms
                                                                  • sleeps 20
                                                                  • min stay varies
                                                                  • Child friendly
                                                                  • Air conditioning
                                                                  Gorgeous new home on the ocean near Boston and Cape Cod. The Lions’ Den is a 4800 square foot gorgeous new home located in Scituate, MA – close to both Boston and Cape Cod. It features incredible views of the ocean with 6 decks and a widow's walk. Best panoramic view i

                                                                  from $1,718 / night

                                                                  $10,305 / week

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                                                                  from $1,718 / night

                                                                    11

                                                                    Boston Vacation apartment rental

                                                                    Massachusetts / Boston

                                                                    2 5 1 night min

                                                                    • 2 bedrooms
                                                                    • sleeps 5
                                                                    • 1 night min
                                                                    • Child friendly
                                                                    • Car not necessary
                                                                    Clean, spacious two bedroom is close to Ashmont Village, UMASS Boston & Downtown Boston. You’ll love the Quiet neighborhood with included off-street parking a short drive, uber or train ride to downtown. My place is good for couples and families. Lots of restaurants and

                                                                    from $218 / night

                                                                    $1,523 / week

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                                                                    Responds fast!
                                                                    avg. 2 hours 18 minutes

                                                                    from $218 / night

                                                                      23

                                                                      Vacation apartment in Boston

                                                                      Massachusetts / Boston

                                                                      1 4 min stay varies

                                                                      • 1 bedroom
                                                                      • sleeps 4
                                                                      • min stay varies
                                                                      • Child friendly
                                                                      • Pet friendly
                                                                      Conveniently located across from premier shopping, dining, and nightlife establishments. You can walk out your to your front door and you’re in walking distance to some of the city’s premier attractions. Easy access to major highways, adjacent to the Silver Line and air

                                                                      from $171 / night

                                                                      $1,195 / week

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                                                                      from $171 / night

                                                                        29

                                                                        Vacation apartment in Boston

                                                                        Massachusetts / Boston

                                                                        1 4 2 nights min

                                                                        • 1 bedroom
                                                                        • sleeps 4
                                                                        • 2 nights 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 14 minutes

                                                                        from $189 / night

                                                                        (7) Very Good 

                                                                          24

                                                                          Vacation home in Boston

                                                                          Massachusetts / Boston

                                                                          3 13 2 nights min

                                                                          • 3 bedrooms
                                                                          • sleeps 13
                                                                          • 2 nights min
                                                                          • Nearest beach 2 mi
                                                                          • Child friendly
                                                                          • Car not necessary
                                                                          • Newly renovated, Sunny and cozy 1000 sq ft •3br/2Ba, living room,large kitchen/dining area & deck/backyard. •Great for families. Business Travellers and group gathering. •Fits 13 •4 miles to BCEC ,downtown •14mn to Logan Airport •Free street pk.Free wifi •12mn to S

                                                                          from $352 / night

                                                                          $2,461 / week

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                                                                          from $352 / night

                                                                            10

                                                                            Vacation home rental

                                                                            Massachusetts / Boston

                                                                            2 8 2 nights min

                                                                            • 2 bedrooms
                                                                            • sleeps 8
                                                                            • 2 nights min
                                                                            • Child friendly
                                                                            This two cozy and comfortable bedroom apartment is located at East Boston close to Logan airport. There is a free shuttle bus between the airport T-station and the airport terminals. only 2 stops away on the T from airport. You’ll love this place as we provide you every

                                                                            from $228 / night

                                                                            $1,489 / week

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                                                                            from $228 / night

                                                                            (2) Excellent 

                                                                              19

                                                                              Apartment rental in Boston

                                                                              Massachusetts / Boston

                                                                              3 10 1 night min

                                                                              • 3 bedrooms
                                                                              • sleeps 10
                                                                              • 1 night min
                                                                              • Child friendly
                                                                              • Air conditioning
                                                                              First floor unit with open floor plan, modern kitchen, 3 bedrooms, 2 full baths and two parking in tandem in a 2-family house. It is located in Oak square, Brighton, Boston. This unit is about 1 mile from Boston College (3 minutes driving, 15 minutes walking). 1 miles

                                                                              from $217 / night

                                                                              $1,515 / week

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                                                                              avg. 2 hours 37 minutes

                                                                              from $217 / night

                                                                              (53) Excellent 

                                                                                23

                                                                                Vacation yacht in Boston

                                                                                Massachusetts / Boston

                                                                                2 6 2 nights min

                                                                                • 2 bedrooms
                                                                                • sleeps 6
                                                                                • 2 nights min
                                                                                • Beach/lakeside relaxation
                                                                                • Air conditioning
                                                                                *** Celebrating 28 Years in Business as Boston's Original B&B Afloat *** If you are looking for an absolutely unique and romantic getaway experience to celebrate a birthday, anniversary, engagement, or wedding, the Golden Slipper awaits. It is an ideal romantic getaway

                                                                                from $315 / night

                                                                                $2,124 - $4,208 / week

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                                                                                from $315 / night

                                                                                  13

                                                                                  Vacation apartment in Boston

                                                                                  Massachusetts / Boston

                                                                                  1 3 4 nights min

                                                                                  • 1 bedroom
                                                                                  • sleeps 3
                                                                                  • 4 nights min
                                                                                  • Child friendly
                                                                                  • Car not necessary
                                                                                  • Air conditioning
                                                                                  Step outside your door and begin your historical tour of Boston. Stop at Modern Bakery for a canoli or piece of Ricotta pie while on your way to Paul Reveres home or the Old North Church just a few blocks from this apartment. Boston is beautiful, rich in history, an

                                                                                  from $229 / night

                                                                                  $1,603 / week

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                                                                                  from $229 / night