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Massachusetts Vacation Rentals(4,313)

4,313 Results
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7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
    (27)
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    2 - 6 night minimum stay
    • 3 BR,
    • 1 BA,
    • Sleeps 6
      (19)
      $1,000 - $1,400
      per night
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      6 - 7 night minimum stay
      • 4 BR,
      • 3 BA,
      • 1 HF BA,
      • Sleeps 14
        (7)
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        1 - 7 night minimum stay
        • 4 BR,
        • 2 BA,
        • 1 HF BA,
        • Sleeps 8
          (7)
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          1 - 7 night minimum stay
          • 4 BR,
          • 3 BA,
          • Sleeps 15
            (5)
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            3 - 7 night minimum stay
            • 7 BR,
            • 6 BA,
            • 1 HF BA,
            • Sleeps 16
              (5)
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              3 - 7 night minimum stay
              • 6 BR,
              • 3 BA,
              • Sleeps 16
                (6)
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                7 night minimum stay
                • 5 BR,
                • 3 BA,
                • Sleeps 12
                  1 Review
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                  7 night minimum stay
                  • 4 BR,
                  • 2 BA,
                  • Sleeps 10
                    (7)
                    $250 - $643
                    per night
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                    3 - 7 night minimum stay
                    • 5 BR,
                    • 3 BA,
                    • 1 HF BA,
                    • Sleeps 12
                      1 Review
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                      2 - 6 night minimum stay
                      • 1 BR,
                      • 1 BA,
                      • Sleeps 3
                        (6)
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                        1 - 2 night minimum stay
                        • 1 BR,
                        • 1 BA,
                        • Sleeps 6
                          (20)
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                          7 night minimum stay
                          • 4 BR,
                          • 2 BA,
                          • Sleeps 10
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                            2 - 7 night minimum stay
                            • 3 BR,
                            • 1 BA,
                            • Sleeps 7
                              2 Reviews
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                              1 - 5 night minimum stay
                              • 2 BR,
                              • 2 BA,
                              • Sleeps 6
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                                7 night minimum stay
                                • 4 BR,
                                • 2 BA,
                                • Sleeps 8
                                  $120 - $250
                                  per night
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                                  2 - 6 night minimum stay
                                  • 2 BR,
                                  • 1 BA,
                                  • Sleeps 5
                                    (3)
                                    3 night minimum stay
                                    • 2 BR,
                                    • 1 BA,
                                    • Sleeps 4
                                      (44)
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                                      3 - 14 night minimum stay
                                      • 4 BR,
                                      • 3 BA,
                                      • 1 HF BA,
                                      • Sleeps 8
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                                        7 night minimum stay
                                        • 5 BR,
                                        • 3 BA,
                                        • Sleeps 9
                                          $500 - $886
                                          per night
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                                          3 - 7 night minimum stay
                                          • 4 BR,
                                          • 3 BA,
                                          • 1 HF BA,
                                          • Sleeps 9
                                            7 night minimum stay
                                            • 5 BR,
                                            • 3 BA,
                                            • Sleeps 10
                                              (21)
                                              2 - 7 night minimum stay
                                              • 3 BR,
                                              • 2 BA,
                                              • Sleeps 8
                                                (8)
                                                Book it Now!
                                                7 night minimum stay
                                                • 3 BR,
                                                • 2 BA,
                                                • 1 HF BA,
                                                • Sleeps 9
                                                  7 night minimum stay
                                                  • 4 BR,
                                                  • 2 BA,
                                                  • Sleeps 10
                                                    1 - 5 night minimum stay
                                                    • 2 BR,
                                                    • 2 BA,
                                                    • Sleeps 6
                                                      7 night minimum stay
                                                      • 5 BR,
                                                      • 3 BA,
                                                      • Sleeps 10
                                                        7 night minimum stay
                                                        • 4 BR,
                                                        • 3 BA,
                                                        • 1 HF BA,
                                                        • Sleeps 8
                                                          7 night minimum stay
                                                          • 4 BR,
                                                          • 4 BA,
                                                          • 1 HF BA,
                                                          • Sleeps 8
                                                            7 night minimum stay
                                                            • 4 BR,
                                                            • 3 BA,
                                                            • Sleeps 8
                                                               

                                                              Recent Massachusetts Reviews

                                                              GREAT VACATION AS USUAL!

                                                              5 of 5
                                                              We have been coming to the Upwind for many years now and are never disappointed. The cottage is well equipped with all the comforts of home, and we thoroughly enjoy our time here. The kitchen has everything you could possibly need for both eating and drinking including a wine fridge and glasses. The views from the upper deck, especially at sunset should not be missed. Whether we eat out at the local restaurants like The Lobster Boat or Captain Parkers or go to the local fish market and get steamers and lobsters to cook at home, we always enjoy the food. Taking in a Cape Cod League ballgame is always on our agenda as well as a whale watch out of P-town. We would highly recommend staying here. We are already planning on returning next year!
                                                              • Submitted: Jul 25, 2014
                                                              • Stayed: Jul 2014

                                                              UNEQUALED ACCOMIDATIONS

                                                              5 of 5
                                                              My family and i have been coming to the vineyard for the last 12 years, and this home by far has been the most comfortable place that we have stayed, with the main living and dinning area being spacious and inviting. This home is a true piece of art, with Impeccable stone work, and craftsmanship throughout. This home accommodated 12 people with ease, with everyone having there own privacy. The house has two main level which is accessible by stairs and elevator, and almost every room is equipped with its very own entertainment system. The grounds are meticulously kept with numerous types of plants and trees, which is situated on a large private lot. This home is centrally placed between vineyard heaven and oaks bluff (5-10 min to each), and 15 min from Edgartown. I would highly recommend this home to anyone that is interested in staying on the vineyard.
                                                              • Submitted: Jul 22, 2014
                                                              • Stayed: Jul 2014

                                                              RELAXING FAMILY VACATION

                                                              5 of 5
                                                              My husband and I, along with our 2 year old daughter had the best family vacation here. The home is beautiful, comfortable and clean. It felt like our own home after 10 minutes of being there. Our daughter loved "her" room and frequently asks to go back to "her" Cape house. The quiet neighborhood was a perfect place for us. My favorite memories were made on our daily walks to the beach, which was such an easy walk that our daughter did it barefoot. Best beach on the Cape for sure! Convenient to food, shopping and the usual touristy cape stuff. If you haven't been to Chatham I highly recommend it. Its our new favorite Cape town(I think we have been to them all!) Linda was an absolute pleasure to work with and made things as easy as possible for us. Unless we buy a house in that same neighborhood for ourselves...we will return to this home again!
                                                              • Submitted: Jul 16, 2014
                                                              • Stayed: Jun 2014