50 Best Massachusetts Apartments on Holiday Lettings - Vacation rentals

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6,512 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

    from $115 / night

    $802 / week

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    avg. 1 hour 35 minutes

    from $115 / night

      52

      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

      from $315 / night

      $1,832 - $5,147 / week

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      avg. 3 hours 18 minutes

      from $315 / 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

        from $457 / night

        $3,607 / week

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        avg. 2 hours 6 minutes

        from $457 / 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

          from $378 / night

          $2,645 / week

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          avg. 2 hours 4 minutes

          from $378 / 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

            from $516 / night

            $3,607 / week

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            avg. 1 hour 21 minutes

            from $516 / night

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              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

              from $234 / night

              $1,635 / week

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              avg. 2 hours 21 minutes

              from $234 / 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

                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

                  from $884 / night

                  $6,183 / week

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                  from $884 / 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

                    from $489 / night

                    $3,422 - $3,822 / week

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                    from $489 / 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

                      from $557 / night

                      $3,893 / week

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                      from $557 / night

                        19

                        B&b rental in Massachusetts

                        Nantucket / Siasconset

                        3 6 1 night min

                        • 3 bedrooms
                        • sleeps 6
                        • 1 night min
                        • Nearest beach 1 mi
                        • 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

                        from $287 / night

                        $2,004 / week

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                        avg. 48 minutes

                        from $287 / 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

                          from $287 / night

                          $2,061 / week

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                          avg. 1 hour 6 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

                              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

                              from $1,011 / night

                              $7,071 / week

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                              from $1,011 / 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

                                from $1,144 / night

                                $8,012 / week

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                                avg. 48 minutes

                                from $1,144 / 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

                                  from $401 / night

                                  $2,806 / week

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                                  from $401 / 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

                                    from $453 / night

                                    $2,863 - $4,008 / week

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                                    from $453 / night

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                                      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.

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                                        70

                                        Provincetown Vacation yacht rental

                                        Cape Cod / Provincetown

                                        3 6 1 night min

                                        • 3 bedrooms
                                        • sleeps 6
                                        • 1 night min
                                        • Child friendly
                                        • Air conditioning
                                        Create lasting memories on an all-inclusive private charter boat for up to 6 people. Enjoy the unique all-inclusive vacation experience of sailing, fishing, paddling, shellfishing, whale watching and exploring the delights of Cape Cod aboard our 47ft luxury sailing cata

                                        from $2,462 / night

                                        $17,233 / week

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                                        from $2,462 / 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

                                          from $246 / night

                                          $1,718 / week

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                                          from $246 / 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

                                            from $344 / night

                                            $2,405 / week

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                                            from $344 / 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

                                              from $483 / night

                                              $3,378 / week

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                                              from $483 / night

                                                8

                                                Vacation home in Brewster

                                                Cape Cod / Brewster

                                                4 9 min stay varies

                                                • 4 bedrooms
                                                • sleeps 9
                                                • min stay varies
                                                • 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

                                                from $516 / night

                                                $3,435 - $4,580 / week

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                                                from $516 / night

                                                  35

                                                  Vacation apartment with shared pool in Boston

                                                  Massachusetts / Boston

                                                  1 4 3 nights min

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

                                                  from $401 / night

                                                  $2,806 / week

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                                                  from $401 / night

                                                    39

                                                    Vacation apartment rental

                                                    Massachusetts / Boston

                                                    2 5 3 nights min

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

                                                    from $573 / night

                                                    $4,008 / week

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                                                    from $573 / night

                                                      10

                                                      Vacation condo rental

                                                      Cape Cod / Hyannis

                                                      1 4 7 nights min

                                                      • 1 bedroom
                                                      • sleeps 4
                                                      • 7 nights min
                                                      • Swimming pool
                                                      • Child friendly
                                                      • Air conditioning
                                                      Let "The Breakwaters" be your vacation home to maximize your Cape Cod experience. This one bedroom, one bath condo comes fully equipped with everything you need for a relaxing vacation. Just steps from Sea Street Beach and minutes from downtown Hyannis and Nantucket and

                                                      from $213 / night

                                                      $1,489 / week

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                                                      from $213 / night

                                                        11

                                                        Hyannis Vacation home rental

                                                        Cape Cod / Hyannis

                                                        2 4 7 nights min

                                                        • 2 bedrooms
                                                        • sleeps 4
                                                        • 7 nights min
                                                        • Child friendly
                                                        • Air conditioning
                                                        • Pet friendly
                                                        A perfect spot for your Cape Cod getaway! This centrally located home features a fully equipped kitchen, dining area, cozy living room, and central air. Enjoy the private back yard while relaxing on the deck after a day at the beach. Home sleeps four on one queen and t

                                                        from $197 / night

                                                        $1,374 / week

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                                                        from $197 / 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

                                                          from $246 / night

                                                          $1,718 / week

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                                                          from $246 / night

                                                            29

                                                            Vacation home in Hyannis

                                                            Cape Cod / Hyannis

                                                            3 7 7 nights min

                                                            • 3 bedrooms
                                                            • sleeps 7
                                                            • 7 nights min
                                                            • Child friendly
                                                            Beautifully renovated with every modern amenity, this antique home is a one of kind place to spend your vacation. Richly decorated yet still comfortable and relaxed, the home features three spacious bedrooms, two full baths and one half bath. The first floor offers a fu

                                                            from $655 / night

                                                            $4,580 / week

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                                                            from $655 / 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

                                                              from $1,288 / night

                                                              $6,438 / week

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                                                              from $1,288 / 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 $1,488 / night

                                                                $7,438 / week

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                                                                from $1,488 / night

                                                                  0

                                                                  Vacation home in Sandwich

                                                                  Cape Cod / Sandwich

                                                                  3 6 min stay varies

                                                                  • 3 bedrooms
                                                                  • sleeps 6
                                                                  • min stay varies
                                                                  • Child friendly
                                                                  • Air conditioning
                                                                  This comfortable house in Cape Cod offers a relaxing family getaway, with partial ocean views from the balcony, a variety of entertainment to keep the kids happy, and a beautiful sandy beach within easy walking distance! The interior has a warm ambiance with a wood floo

                                                                  from $147 / night

                                                                  $1,026 / week

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                                                                  avg. 1 hour 58 minutes

                                                                  from $147 / night

                                                                    15

                                                                    Vacation condo rental

                                                                    Dennis / Dennis Port

                                                                    1 4 min stay varies

                                                                    • 1 bedroom
                                                                    • sleeps 4
                                                                    • min stay varies
                                                                    • Child friendly
                                                                    Adorable condo with ocean views! We are across the street from Glendon Beach, the waves and sand are less than 500 feet away! Condo was freshly renovated and updated this spring. Condo has one bedroom with a queen bed and a full size futon in the living room that sleeps

                                                                    from $144 / night

                                                                    $1,489 / week

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                                                                    avg. 2 hours 17 minutes

                                                                    from $144 / night

                                                                      25

                                                                      Vacation home in Dennis

                                                                      Cape Cod / Dennis

                                                                      5 10 min stay varies

                                                                      • 5 bedrooms
                                                                      • sleeps 10
                                                                      • 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 10, 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

                                                                      from $687 / night

                                                                      $4,809 / week

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                                                                      avg. 19 minutes

                                                                      from $687 / night

                                                                        18

                                                                        Vacation home in Siasconset

                                                                        Nantucket / Siasconset

                                                                        4 8 7 nights min

                                                                        • 4 bedrooms
                                                                        • sleeps 8
                                                                        • 7 nights min
                                                                        • Beach/lakeside relaxation
                                                                        • Child friendly
                                                                        • Air conditioning
                                                                        This newly restored International Style home has a large living room with dining area (seats 8 to 10) facing ocean, fully equipped modern kitchen, first floor bedroom with private bath and sitting room. Lower floor has three additional bedrooms and baths, den, laundry r

                                                                        from $1,072 / night

                                                                        $7,500 - $14,500 / week

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                                                                        from $1,072 / night

                                                                          16

                                                                          Home rental in Massachusetts

                                                                          Massachusetts / Cohasset

                                                                          4 8 7 nights min

                                                                          • 4 bedrooms
                                                                          • sleeps 8
                                                                          • 7 nights min
                                                                          • Beach/lakeside relaxation
                                                                          • Child friendly
                                                                          • Air conditioning
                                                                          This 4 BR, 3 BA roomy home has magnificent views of the ocean, steps to Sandy Cove (a private beach), and comes fully furnished and available for weekly summer rentals. Why sit in Cape traffic when you can make your summer vacation destination here? Bring your sunscreen

                                                                          from $745 / night

                                                                          $5,153 / week

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                                                                          from $745 / night

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                                                                            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.

                                                                            from $132 / night

                                                                            $897 - $2,528 / week

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                                                                            avg. 1 hour 42 minutes

                                                                            from $132 / night

                                                                              15

                                                                              Chatham Vacation home accommodation

                                                                              Cape Cod / Chatham

                                                                              4 8 min stay varies

                                                                              • 4 bedrooms
                                                                              • sleeps 8
                                                                              • min stay varies
                                                                              • Child friendly
                                                                              • 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

                                                                              from $171 / night

                                                                              $1,200 - $2,200 / week

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                                                                              from $171 / 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

                                                                                from $201 / night

                                                                                $1,260 - $1,661 / week

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                                                                                from $201 / night

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                                                                                  8

                                                                                  Vacation b&b rental

                                                                                  Massachusetts / Arlington

                                                                                  1 2 1 night min

                                                                                  • 1 bedroom
                                                                                  • sleeps 2
                                                                                  • 1 night min
                                                                                  Nicely appointed room in home with double bed, keurig coffee maker, fridge, and microwave. Shared bathroom. Lovely outdoor living areas with grill and hammock! 1 minute walk to bus, 5 minute walk to restaurants. 10 minute drive to Harvard Square. A friendly kitty lives

                                                                                  from $86 / night

                                                                                  $573 / week

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                                                                                  from $86 / night

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