50 Best Massachusetts Apartments on Holiday Lettings - Vacation rentals

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5,784 Vacation rentals

    10

    Massachusetts Vacation apartment rental

    Massachusetts / Beverly

    3 5 1 night min

    • 3 bedrooms
    • sleeps 5
    • 1 night min
    • Child friendly
    • Car not necessary
    Fabulous 2 bedroom located in the heart of downtown Beverly. Clean and comfortable. 5min drive to downtown Salem,ma. Walking distance from restaurants, bars, Beverly nightlife. Near Salem harbor, museums, Salem Willows (family game center), Salem State College, Endico …see more

    from $115 / night

    $802 / week

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    from $115 / night

      51

      Vacation home in South Chatham

      Chatham / South Chatham

      3 10 min stay varies

      • 3 bedrooms
      • sleeps 10
      • min stay varies
      • Nearest beach 0.6 mi
      • Child friendly
      • Air conditioning
      Newly renovated kitchen with quartz “Sea Glass” countertops, backsplash and Nantucket farm sink. Truly a well equipped cooks kitchen. This year round low allergen, open concept home has 3 bedrooms, 2 newly updated baths, a large two level outdoor deck with electric ret …see more

      from $315 / night

      $1,832 - $5,147 / week

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      avg. 2 hours 15 minutes

      from $315 / night

        18

        Home rental in Massachusetts

        Massachusetts / Marblehead

        3 6 4 nights min

        • 3 bedrooms
        • sleeps 6
        • 4 nights min
        • Child friendly
        • Air conditioning
        • Pet friendly
        Home originally built in 1923. Purchased and completely renovated in 2004. 1600 sq. ft. As you step onto a mahogany front porch, you open a walnut wood front door into a spacious open floor plan. Diningroom, livingroom and kitchen are bright and cheerful. First floor …see more

        from $378 / night

        $2,645 / week

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        avg. 2 hours 4 minutes

        from $378 / night

        (3) Excellent 

          24

          Vacation apartment rental

          Massachusetts / Plymouth

          1 4 min stay varies

          • 1 bedroom
          • sleeps 4
          • min stay varies
          • Beach/lakeside relaxation
          • Nearest beach 0.5 mi
          • Child friendly
          A beautiful one-bedroom with additional queen sleep-sofa in the heart of historic Plymouth harbor is waiting for you. Not more than 15 yards to the water and a 3-minute walk to the Mayflower and Plymouth Rock, this location couldn't be better for a vacation rental in P …see more

          from $269 / night

          $1,489 - $2,061 / week

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          from $269 / night

            23

            Vacation home in Massachusetts

            Massachusetts / Plum Island

            4 8 7 nights min

            • 4 bedrooms
            • sleeps 8
            • 7 nights min
            • Child friendly
            • Air conditioning
            Coveted Oceanfront at the Entrance of the Merrimac River. Enjoy 3 levels of decks as you watch the boats pass thru the Breakers. Enjoy panoramic views from the rooftop deck from the coastline of Maine & New Hampshire North to the Isles of Shoal East to Rockport & Glouce …see more

            from $457 / night

            $3,607 / week

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            avg. 2 hours 6 minutes

            from $457 / night

            (14) Very Good 

              19

              Vacation home in Eastham

              Cape Cod / Eastham

              4 8 7 nights min

              • 4 bedrooms
              • sleeps 8
              • 7 nights min
              • Beach/lakeside relaxation
              • Child friendly
              • Air conditioning
              Cosy, welcoming home in South Eastham on the outer Cape. The property is well equipped and with lots of space for families or groups. Our traditional Cape Cod house features 4 bedrooms, 2 baths, a generous open plan living/dining/kitchen leading out to a deck. The hous …see more

              from $234 / night

              $1,635 / week

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              avg. 2 hours 19 minutes

              from $234 / night

                31

                Vacation home with golf nearby in Stockbridge

                Berkshires / Stockbridge

                4 9 min stay varies

                • 4 bedrooms
                • sleeps 9
                • min stay varies
                • Child friendly
                • Air conditioning
                • Pet friendly
                THE ESCAPE at Stockbridge. Enjoy our Open & Spacious Newly built house in the Berkshires, Complete Privacy! No Visible Neighbors. -1 1/2 miles to downtown Stockbridge, -just minutes to Norman Rockwell museum, Chesterwood, Naumkeag, Tanglewood & Kripalu. -Housatonic R …see more

                from $516 / night

                $3,607 / week

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                avg. 1 hour 21 minutes

                from $516 / night

                  52

                  Vacation home in Centerville

                  Cape Cod / Centerville

                  2 6 7 nights min

                  • 2 bedrooms
                  • sleeps 6
                  • 7 nights min
                  • Beach/lakeside relaxation
                  • Nearest beach 0 mi
                  • Child friendly
                  Close your eyes and imagine the perfect beach house .Well that's what Mc's Shack Beach House . Situated down a leafy lane right on the beach, on your own private stretch of beach. Mc's Shack Beach House is approx 1700 sq ft ,it has 2 large bedrooms ,a large livingro …see more

                  from $489 / night

                  $3,422 - $3,822 / week

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                  from $489 / night

                    13

                    Cottage rental in Dennis Port

                    Dennis / Dennis Port

                    2 6 5 nights min

                    • 2 bedrooms
                    • sleeps 6
                    • 5 nights min
                    • Child friendly
                    • Air conditioning
                    • Private garden
                    Welcome to Stone's Throw, just steps from the warm waters of Nantucket Sound! Under new ownership for the 2018 season! Two bedroom, one bathroom rental unit at the Stone's Throw property. Just a "Stone's Throw" to popular Sea Street Beach on Nantucket Sound. Also enjoy …see more

                    from $275 / night

                    $1,718 / week

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                    from $275 / night

                      20

                      Massachusetts Vacation home rental

                      Massachusetts / Nantucket

                      4 7 7 nights min

                      • 4 bedrooms
                      • sleeps 7
                      • 7 nights min
                      • Beach/lakeside relaxation
                      • Nearest beach 1 mi
                      • Child friendly
                      This classic and historic Nantucket sea captain's house (part of Nantucket's Historic Registry) was built in 1807 is located on Nantucket Island lying east of Cape Cod, Massachusetts, easily accessible from Boston. Carefully restored by its owners, the home is a short …see more

                      from $884 / night

                      $6,183 / week

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                      from $884 / night

                        14

                        Provincetown Vacation condo rental

                        Cape Cod / Provincetown

                        2 4 7 nights min

                        • 2 bedrooms
                        • sleeps 4
                        • 7 nights min
                        • Beach/lakeside relaxation
                        • Air conditioning
                        • Private garden
                        A rare historic gem located in Provincetown's Gallery District at the top of Pearl St. This exclusive unit is one of two redeveloped from a 19th-century barn that later served as the Cape School of Art and the studio and residence of the American painter Edwin Dickinson …see more

                        from $557 / night

                        $3,893 / week

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                        from $557 / night

                          20

                          Home rental in Orleans

                          Cape Cod / Orleans

                          4 6 3 nights min

                          • 4 bedrooms
                          • sleeps 6
                          • 3 nights min
                          • Child friendly
                          • Air conditioning
                          Our home is located in a quiet upscale neighbourhood close to all amenities. Walk to grocery store, downtown shopping, library, tennis courts and town field. Less than a 5 minute drive to ocean and bay. Quick access to highway and all the surrounding Cape towns. Rel …see more

                          from $287 / night

                          $2,061 / week

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                          avg. 53 minutes

                          from $287 / night

                            19

                            B&b rental in Massachusetts

                            Nantucket / Siasconset

                            3 6 1 night min

                            • 3 bedrooms
                            • sleeps 6
                            • 1 night min
                            • Child friendly
                            • Air conditioning
                            Sea Lion is a 4 bedroom house located in the heart of Tom Nevers. In the summer it's a holiday rental house, in the winter I transform it into a Bed & Breakfast, and live on-site as your hostess. Space Sea Lion is a classic Tom Nevers Upside Down House with 4 decks and …see more

                            from $287 / night

                            $2,004 / week

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                            Responds fast!
                            avg. 55 minutes

                            from $287 / night

                              4

                              Apartment rental in Massachusetts

                              Massachusetts / Cambridge

                              2 4 1 night min

                              • 2 bedrooms
                              • sleeps 4
                              • 1 night min
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                              from $12 / night

                              $81 / week

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                              from $12 / night

                                4

                                Home rental in Somerville

                                Massachusetts / Somerville

                                3 10 2 nights min

                                • 3 bedrooms
                                • sleeps 10
                                • 2 nights min
                                • Child friendly
                                • Car not necessary
                                • Air conditioning
                                Our 3 bed, 2 bath, townhouse is business ready with wifi, 50inch tv with full cable, keurig & coffee/tea and flexible check-ins. We have a stock of DVDs, blowdryer, iron, universal charging station, a collection of frequent forgettables from all our travels, and hand w …see more

                                from $401 / night

                                $2,806 / week

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                                from $401 / night

                                  29

                                  Home rental in Massachusetts

                                  Nantucket / Siasconset

                                  4 8 3 nights min

                                  • 4 bedrooms
                                  • sleeps 8
                                  • 3 nights min
                                  • Child friendly
                                  • Air conditioning
                                  • Private garden
                                  Nantucket is a magical little island located 30 miles off the shores of Cape Cod. It's steeped in the history of its whaling founding fathers. Grey shingled houses dot the coastline, the streets in town are paved in cobblestones, and the harbor is filled with boats well …see more

                                  from $1,144 / night

                                  $8,012 / week

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                                  Responds fast!
                                  avg. 55 minutes

                                  from $1,144 / night

                                    5

                                    Vacation home rental

                                    Martha's Vineyard / Oak Bluffs

                                    4 7 7 nights min

                                    • 4 bedrooms
                                    • sleeps 7
                                    • 7 nights min
                                    • Nearest beach 1 mi
                                    • Child friendly
                                    Nestled in Historical Oak Bluffs is our one level cottage. It features a large (15x37) deck. Location. location. 1.5 miles from either ferry. Oak Bluffs or Vineyard Haven. . Distance to shopping , either town or going to the beach less then 1 mile. Public transportation …see more

                                    from $453 / night

                                    $2,863 - $4,008 / week

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                                    from $453 / night

                                      6

                                      Massachusetts Vacation townhouse rental

                                      Martha's Vineyard / Edgartown

                                      3 8 7 nights min

                                      • 3 bedrooms
                                      • sleeps 8
                                      • 7 nights min
                                      • Child friendly
                                      • Pet friendly
                                      The K-4 Duplex is part of the Winnetu Oceanside Resort - the only Resort at South Beach. It's a 10-minute walk to the beach and is situated at the bicycling/jogging path leading to charming Edgartown. This 'Silver Level' home offers three bedrooms, two-and-a-half bathro …see more

                                      from $1,011 / night

                                      $7,071 / week

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                                      from $1,011 / night

                                        8

                                        Vacation home in Brewster

                                        Cape Cod / Brewster

                                        4 9 5 nights min

                                        • 4 bedrooms
                                        • sleeps 9
                                        • 5 nights min
                                        • Child friendly
                                        • Air conditioning
                                        • Pet friendly
                                        Home located on Nickerson State Park, right near Cape Cod Bike Trail entrances, and about 1.5 miles from 6A beautiful beaches. Huge yard in private neighborhood. Plenty of space for cookouts, fire pit in yard. Trails into Nickerson State Park. 4 bedrooms, plenty of extr …see more

                                        from $630 / night

                                        $3,435 / week

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                                        from $630 / night

                                          13

                                          Vacation home in Hyannis

                                          Cape Cod / Hyannis

                                          4 8 7 nights min

                                          • 4 bedrooms
                                          • sleeps 8
                                          • 7 nights min
                                          • Child friendly
                                          • Air conditioning
                                          • Private garden
                                          Modern Cape Charm abounds from this beach house just 1/10th of a mile from Keyes Beach. Located minutes from historic Main Street, the Kennedy Compound in Hyannis Port and Hyannis Harbor this is the perfect Cape Cod location. Home features and updated galley kitchen tha …see more

                                          from $483 / night

                                          $3,378 / week

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                                          from $483 / night

                                            36

                                            Vacation apartment with shared pool in Massachusetts

                                            Massachusetts / Boston

                                            2 5 3 nights min

                                            • 2 bedrooms
                                            • sleeps 5
                                            • 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 …see more

                                            from $367 / night

                                            $2,565 / week

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                                            from $367 / night

                                              25

                                              Vacation apartment in Massachusetts

                                              Massachusetts / Boston

                                              1 3 3 nights min

                                              • 1 bedroom
                                              • sleeps 3
                                              • 3 nights min
                                              • Child friendly
                                              • Air conditioning
                                              Located in the Downtown area, Boston’s Chinatown is a real gem of a neighborhood packed with tons of nooks and crannies waiting to be explored. It is rich with history, tradition, excitement, gifts, culture, and great food. You can find markets filled with Chinese spec …see more

                                              from $327 / night

                                              $2,285 / week

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                                              from $327 / night

                                                10

                                                Vacation home rental

                                                Cape Cod / Hyannis

                                                3 8 7 nights min

                                                • 3 bedrooms
                                                • sleeps 8
                                                • 7 nights min
                                                • Child friendly
                                                This charming Cape home offers the best in in town location and beach proximity. Just moments from historic Main Street and Cape Cod's commercial center this property offers ease of access to many of the Capes best attractions and its just a few minutes drive to several …see more

                                                from $246 / night

                                                $1,718 / week

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                                                from $246 / night

                                                  16

                                                  South Yarmouth Vacation home rental

                                                  Yarmouth / South Yarmouth

                                                  3 6 7 nights min

                                                  • 3 bedrooms
                                                  • sleeps 6
                                                  • 7 nights min
                                                  • Child friendly
                                                  • Air conditioning
                                                  • Private garden
                                                  This quintessential Cape Cod home is a short walk to Long Pond and Bass River. The home features three bedrooms, two full bathrooms, living room, dining area and kitchen. The exterior offers a beautiful yard and lovely area for relaxing after a day at the beach. Central …see more

                                                  from $246 / night

                                                  $1,718 / week

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                                                  from $246 / night

                                                    15

                                                    Apartment rental in Boston

                                                    Massachusetts / Boston

                                                    2 5 3 nights min

                                                    • 2 bedrooms
                                                    • sleeps 5
                                                    • 3 nights min
                                                    • Child friendly
                                                    • Air conditioning
                                                    South Boston, was once a predominantly Irish Catholic neighborhood. With the development of hotels, restaurants and shopping surrounding the Boston Convention & Exhibition Center (the BCEC), the community is now attracting families and young professionals. A traditional …see more

                                                    from $367 / night

                                                    $2,565 / week

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                                                    from $367 / night

                                                      35

                                                      Vacation studio with shared pool in Massachusetts

                                                      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 …see more

                                                      from $287 / night

                                                      $2,004 / week

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                                                      from $287 / night

                                                      (1) Good 

                                                        6

                                                        Vacation apartment in Massachusetts

                                                        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. …see more

                                                        Pricing unknown

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                                                          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 …see more

                                                          from $298 / night

                                                          $2,084 / week

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                                                          from $298 / night

                                                            17

                                                            Apartment rental in Orleans

                                                            Cape Cod / Orleans

                                                            2 4 6 nights min

                                                            • 2 bedrooms
                                                            • sleeps 4
                                                            • 6 nights min
                                                            • Child friendly
                                                            • Air conditioning
                                                            • Pet friendly
                                                            2 bedroom 1 bath apartment with separate private entrance, driveway and deck. Living room, kitchen, and laundry. Queen bed in one room and a double bed in the other room. Optional air mattress can be set up in living room to sleep 2 more if needed. Window AC units in b …see more

                                                            from $201 / night

                                                            $1,403 / week

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                                                            from $201 / night

                                                              4

                                                              Vacation apartment in Massachusetts

                                                              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 …see more

                                                              from $1,301 / night

                                                              $6,505 / week

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                                                              from $1,301 / 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 …see more

                                                                from $1,479 / night

                                                                $7,395 / week

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                                                                from $1,479 / night

                                                                  29

                                                                  Home rental in Wellfleet

                                                                  Cape Cod / Wellfleet

                                                                  2 5 min stay varies

                                                                  • 2 bedrooms
                                                                  • sleeps 5
                                                                  • min stay varies
                                                                  • Child friendly
                                                                  • Air conditioning
                                                                  *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. …see more

                                                                  from $119 / night

                                                                  $805 - $2,167 / week

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                                                                  avg. 2 hours 24 minutes

                                                                  from $119 / night

                                                                    12

                                                                    Dennis Port Vacation home rental

                                                                    Dennis / Dennis Port

                                                                    3 4 7 nights min

                                                                    • 3 bedrooms
                                                                    • sleeps 4
                                                                    • 7 nights min
                                                                    • Child friendly
                                                                    • Air conditioning
                                                                    • Pet friendly
                                                                    This cute and cozy cottage is equipped with modern amenities. Pets will be considered. The kitchen is fully equipped with a stove, oven, refrigerator, microwave and leads out to a small deck and a large private yard with a gas grill along with a table and chairs. It has …see more

                                                                    from $138 / night

                                                                    $974 / week

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                                                                    Responds fast!
                                                                    avg. 13 minutes

                                                                    from $138 / night

                                                                      25

                                                                      Vacation home in Dennis

                                                                      Cape Cod / Dennis

                                                                      5 13 min stay varies

                                                                      • 5 bedrooms
                                                                      • sleeps 13
                                                                      • min stay varies
                                                                      • Child friendly
                                                                      • Air conditioning
                                                                      • Pet friendly
                                                                      Escape to the beautiful Cape Cod area and stay at this lovely 5-bed, 2.5-bath home, which sleeps 13, in East Dennis. Situated on Cape Cod Bay, just a short walk from a private beach, this ideally located vacation rental offers a plethora of water activities right outsid …see more

                                                                      from $687 / night

                                                                      $4,809 / week

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                                                                      Responds fast!
                                                                      avg. 8 minutes

                                                                      from $687 / night

                                                                      (1) Excellent 

                                                                        28

                                                                        Home rental in Wellfleet

                                                                        Cape Cod / Wellfleet

                                                                        3 5 min stay varies

                                                                        • 3 bedrooms
                                                                        • sleeps 5
                                                                        • min stay varies
                                                                        • Child friendly
                                                                        • Air conditioning
                                                                        *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. …see more

                                                                        from $138 / night

                                                                        $939 - $2,528 / week

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                                                                        Responds fast!
                                                                        avg. 2 hours 24 minutes

                                                                        from $138 / night

                                                                          15

                                                                          Chatham Vacation home accommodation

                                                                          Cape Cod / Chatham

                                                                          4 8 min stay varies

                                                                          • 4 bedrooms
                                                                          • sleeps 8
                                                                          • min stay varies
                                                                          • Ask about children
                                                                          • Air conditioning
                                                                          2019 Rental Rates (Cleaning Fee Included): In-Season: $2,400 per week Off-Season: $1,400 per week Click for More Photos, Map, and Availability Calendar Light and bright 4 BR home, in a great central location! This recently updated home is across from the school tennis c …see more

                                                                          from $171 / night

                                                                          $1,200 - $2,200 / week

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                                                                          from $171 / night

                                                                            12

                                                                            Home rental in Osterville

                                                                            Cape Cod / Osterville

                                                                            3 6 1 night min

                                                                            • 3 bedrooms
                                                                            • sleeps 6
                                                                            • 1 night min
                                                                            • Ask about children
                                                                            • Ask about pets
                                                                            In desirable Wianno Circle location of Osterville. Close to Dowses Beach and village. Great location for this three bedroom, two full bath home. Deck, large yard with gas grill and patio set. New for 2017: central air. Beach pass is provided. ***Subject to all applicab …see more

                                                                            from $385 / night

                                                                            $2,700 / week

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                                                                            from $385 / night

                                                                            (1) Excellent 

                                                                              6

                                                                              Essex Vacation apartment rental

                                                                              Cape Ann / Essex

                                                                              1 4 2 nights min

                                                                              • 1 bedroom
                                                                              • sleeps 4
                                                                              • 2 nights min
                                                                              • Child friendly
                                                                              • Air conditioning
                                                                              • Pet friendly
                                                                              We can now offer Apartment B to our options at Cedar Hill Farm B & B. This apartment is identical to Apt. A also located in our lower barn. The bedroom is on second floor with open to living area and cathedral ceiling. 8 Foot sliders open to open pastures, woods and …see more

                                                                              from $201 / night

                                                                              $1,260 - $1,661 / week

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                                                                              from $201 / night

                                                                                24

                                                                                Chatham Vacation home accommodation

                                                                                Cape Cod / Chatham

                                                                                4 8 7 nights min

                                                                                • 4 bedrooms
                                                                                • sleeps 8
                                                                                • 7 nights min
                                                                                • Ask about children
                                                                                • Air conditioning
                                                                                • Pet friendly
                                                                                Walk to the beach from this in-town location. This recently renovated 4 bedroom 2.5 bathroom cottage received the Chatham Preservation Award in 2010. The home boasts gleaming hardwood floors, an updated kitchen and two separate living areas. There is a sunken master …see more

                                                                                from $571 / night

                                                                                $4,000 / week

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                                                                                from $571 / night

                                                                                  9

                                                                                  Cotuit Vacation home rental

                                                                                  Cape Cod / Cotuit

                                                                                  3 8 7 nights min

                                                                                  • 3 bedrooms
                                                                                  • sleeps 8
                                                                                  • 7 nights min
                                                                                  • Beach/lakeside relaxation
                                                                                  • Nearest beach 0.02 mi
                                                                                  • Child friendly
                                                                                  This charming Cape house is 202 years old, and was the original home of Captain Nickerson of Cotuit. Gracefully restored to modern demands, the house is one and a half blocks from the beach. A brand new kitchen is featured in this lovely old cape house, 200 year- old …see more

                                                                                  from $287 / night

                                                                                  $2,290 - $2,863 / week

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                                                                                  from $287 / night

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