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  • Showing 1-50 of 300+
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    Excellent! 4.6/5
    (16 reviews)
    avg/night
    • 2 BR
    • 1 BA
    • Sleeps 5
    House #122780
    16
    Viewed 41 times in the last 48 hours
      Excellent! 4.7/5
      (22 reviews)
      avg/night
      • 4 BR
      • 1 BA
      • Sleeps 10
      Barn #346642vb
      22
      Viewed 50 times in the last 48 hours
        Wonderful! 4.9/5
        (17 reviews)
        avg/night
        • 2 BR
        • 1 BA
        • Sleeps 6
        Cottage #300900
        17
        Viewed 50 times in the last 48 hours
          avg/night
          • 2 BR
          • 2 BA
          • Sleeps 8
          Condo #907348vb
          0
          Viewed 53 times in the last 48 hours
            Wonderful! 4.9/5
            (14 reviews)
            avg/night
            • 5 BR
            • 3 BA
            • Sleeps 10
            House #603552vb
            14
            Viewed 36 times in the last 48 hours
              avg/night
              • 2 BR
              • 2 BA
              • Sleeps 8
              Condo #4281302
              1
              Viewed 22 times in the last 48 hours
                • 5 BR
                • 2 BA
                • 1 HF BA
                • Sleeps 9
                House #923513vb
                3
                Viewed 37 times in the last 48 hours
                  • 2 BR
                  • 2 BA
                  • Sleeps 8
                  Condo #724286vb
                  2
                  Viewed 41 times in the last 48 hours
                    Exceptional! 5.0/5
                    (26 reviews)
                    avg/night
                    • 2 BR
                    • 2 BA
                    • Sleeps 6
                    Condo #651723vb
                    26
                    Viewed 26 times in the last 48 hours
                      avg/night
                      • 6 BR
                      • 3 BA
                      • 1 HF BA
                      • Sleeps 17
                      House #937764
                      10
                      Viewed 40 times in the last 48 hours
                        $87
                        avg/night
                        • 2 BR
                        • 2 BA
                        • Sleeps 8
                        Condo #650023vb
                        1
                        Viewed 40 times in the last 48 hours
                          • 2 BR
                          • 2 BA
                          • Sleeps 8
                          Condo #3815326
                          0
                          Viewed 18 times in the last 48 hours
                            Exceptional! 5.0/5
                            (46 reviews)
                            avg/night
                            • 3 BR
                            • 2 BA
                            • Sleeps 8
                            Condo #575909vb
                            46
                            Viewed 115 times in the last 48 hours
                              Exceptional! 5.0/5
                              (10 reviews)
                              avg/night
                              • 2 BR
                              • 2 BA
                              • Sleeps 6
                              Condo #786429vb
                              10
                              Viewed 34 times in the last 48 hours
                                Wonderful! 4.9/5
                                (11 reviews)
                                avg/night
                                • 1 BR
                                • 1 BA
                                • Sleeps 4
                                Apartment #129461vb
                                11
                                Viewed 11 times in the last 48 hours
                                  Exceptional! 5.0/5
                                  (7 reviews)
                                  avg/night
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 8
                                  Condo #105168
                                  7
                                  Viewed 17 times in the last 48 hours
                                    avg/night
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 4
                                    Condo #664124vb
                                    0
                                    Viewed 12 times in the last 48 hours
                                      avg/night
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 4
                                      Condo #663246vb
                                      0
                                      Viewed 5 times in the last 48 hours
                                        Viewed 16 times in the last 48 hours
                                          Wonderful! 4.9/5
                                          (8 reviews)
                                          avg/night
                                          • 3 BR
                                          • 2 BA
                                          • 1 HF BA
                                          • Sleeps 9
                                          House #122527
                                          8
                                          Viewed 12 times in the last 48 hours
                                            Wonderful! 4.9/5
                                            (27 reviews)
                                            avg/night
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 12
                                            House #420727vb
                                            27
                                            Viewed 33 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (10 reviews)
                                              avg/night
                                              • 4 BR
                                              • 2 BA
                                              • 1 HF BA
                                              • Sleeps 8
                                              Farmhouse #627684vb
                                              10
                                              Viewed 14 times in the last 48 hours
                                                avg/night
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 8
                                                Condo #224073
                                                2
                                                Viewed 5 times in the last 48 hours
                                                  Exceptional! 5.0/5
                                                  (6 reviews)
                                                  avg/night
                                                  • 4 BR
                                                  • 3 BA
                                                  • 1 HF BA
                                                  • Sleeps 8
                                                  House #3661207
                                                  6
                                                  Viewed 45 times in the last 48 hours
                                                    avg/night
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 8
                                                    Condo #925349vb
                                                    0
                                                    Viewed 5 times in the last 48 hours
                                                      Excellent! 4.7/5
                                                      (6 reviews)
                                                      avg/night
                                                      • 6 BR
                                                      • 2 BA
                                                      • Sleeps 13
                                                      House #7060428
                                                      6
                                                      Viewed 12 times in the last 48 hours
                                                        Wonderful! 4.9/5
                                                        (23 reviews)
                                                        avg/night
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 6
                                                        House #3011344
                                                        23
                                                        Viewed 36 times in the last 48 hours
                                                          • 4 BR
                                                          • 2 BA
                                                          • 1 HF BA
                                                          • Sleeps 8
                                                          House #956972vb
                                                          0
                                                          Viewed 7 times in the last 48 hours
                                                            Wonderful! 4.9/5
                                                            (7 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            House #3836464
                                                            7
                                                            Viewed 34 times in the last 48 hours
                                                              Wonderful! 4.8/5
                                                              (13 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 1 BA
                                                              • Sleeps 4
                                                              Cottage #962761
                                                              13
                                                              Viewed 14 times in the last 48 hours
                                                                Exceptional! 5.0/5
                                                                (16 reviews)
                                                                avg/night
                                                                • 3 BR
                                                                • 1 BA
                                                                • 1 HF BA
                                                                • Sleeps 8
                                                                House #3811779
                                                                16
                                                                Viewed 26 times in the last 48 hours
                                                                  avg/night
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 6
                                                                  Cottage #7079868
                                                                  0
                                                                  Viewed 6 times in the last 48 hours
                                                                    Wonderful! 4.8/5
                                                                    (23 reviews)
                                                                    avg/night
                                                                    • 7 BR
                                                                    • 3 BA
                                                                    • Sleeps 18
                                                                    House #251195vb
                                                                    23
                                                                    Viewed 68 times in the last 48 hours
                                                                      • Studio
                                                                      • 1 BA
                                                                      • Sleeps 2
                                                                      Hotel #3905417
                                                                      0
                                                                        • 3 BR
                                                                        • 1 BA
                                                                        • Sleeps 6
                                                                        Apartment #901029vb
                                                                        1
                                                                          avg/night
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 8
                                                                          Condo #620198vb
                                                                          0
                                                                          Viewed 5 times in the last 48 hours
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 5 BA
                                                                            • 2 HF BA
                                                                            • Sleeps 14
                                                                            House #928559vb
                                                                            0
                                                                            Viewed 39 times in the last 48 hours
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 10
                                                                              House #471272vb
                                                                              0
                                                                              Viewed 8 times in the last 48 hours
                                                                                • 2 BR
                                                                                • 2 BA
                                                                                • Sleeps 8
                                                                                Condo #784788vb
                                                                                1
                                                                                Viewed 9 times in the last 48 hours
                                                                                  avg/night
                                                                                  • 2 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 9
                                                                                  Condo #4022419
                                                                                  1
                                                                                  Viewed 13 times in the last 48 hours
                                                                                    Exceptional! 5.0/5
                                                                                    (6 reviews)
                                                                                    avg/night
                                                                                    • 5 BR
                                                                                    • 5 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 10
                                                                                    House #857164vb
                                                                                    6
                                                                                    Viewed 16 times in the last 48 hours
                                                                                      Excellent! 4.4/5
                                                                                      (10 reviews)
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 4
                                                                                      Cabin #395895
                                                                                      10
                                                                                      Viewed 16 times in the last 48 hours
                                                                                        Wonderful! 4.8/5
                                                                                        (23 reviews)
                                                                                        avg/night
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        House #310035vb
                                                                                        23
                                                                                        Viewed 15 times in the last 48 hours
                                                                                          • 5 BR
                                                                                          • 3 BA
                                                                                          • 2 HF BA
                                                                                          • Sleeps 9
                                                                                          Estate #802737vb
                                                                                          1
                                                                                          Viewed 8 times in the last 48 hours
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 8
                                                                                            Condo #818553vb
                                                                                            0
                                                                                            Viewed 12 times in the last 48 hours
                                                                                              Excellent! 4.4/5
                                                                                              (11 reviews)
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              House #3860654
                                                                                              11
                                                                                              Viewed 31 times in the last 48 hours
                                                                                                avg/night
                                                                                                • 4 BR
                                                                                                • 2 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 8
                                                                                                House #688208vb
                                                                                                3
                                                                                                Viewed 17 times in the last 48 hours
                                                                                                  Excellent! 4.7/5
                                                                                                  (19 reviews)
                                                                                                  avg/night
                                                                                                  • 4 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 8
                                                                                                  House #118052
                                                                                                  19
                                                                                                  Viewed 60 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (8 reviews)
                                                                                                    avg/night
                                                                                                    • 4 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 8
                                                                                                    House #579045vb
                                                                                                    8
                                                                                                    Viewed 21 times in the last 48 hours
                                                                                                      • 3 BR
                                                                                                      • 1 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 5
                                                                                                      Apartment #900625vb
                                                                                                      0
                                                                                                      • 1 - 50 of 300+

                                                                                                      Cheshire: Houses, Condos & More (300+)

                                                                                                       

                                                                                                      Recent Cheshire Reviews

                                                                                                      Great place, very large and comfortable

                                                                                                      5 of 5
                                                                                                      Was much larger than I expected for a one bedroom. Perfect View of Jiminy Peak. Will stay there again I hope.
                                                                                                      • Submitted: Jan 4, 2017
                                                                                                      • Stayed: Dec 2016

                                                                                                      Great stay for two day getaway to the Berkshires

                                                                                                      4 of 5
                                                                                                      We just returned from our 2 day stay at this property. The booking process was straightforward and the owner answered any questions we had promptly. We had two families (4 adults and 6 children). Upon arrival we found the home clean and as described. It fit us all perfectly and we had a great time staying at this property. There are 4 bedrooms, 3 similarly sized bedrooms with queen beds, closets and dressers in which to put our clothing. There is a smaller bedroom with bunk beds and the bottom bunk has a trundle which can be pulled out. Also with a dresser and closet. All bedrooms had plenty of pillows and blankets (Bring your own sheets and pillowcases-we knew this in advance). All bedrooms are on the 2nd floor, there is a wooden gate at the top of the stairs to keep little ones from falling. The upstairs bathroom has a stand up shower (no bathtub), however the downstairs bathroom has a tub (Bring your own towels). On the first floor, there is a three season porch which we used for getting to the backyard to allow the children to play in the snow. This is not heated but it was covered and very spacious-would be a great additional living space/hang out space in the warmer months. The dining room table has two eaves that allow ample seating (we all sat at the table-but they need a few folding chairs to allow that amount of seating at the table). The kitchen was stocked with dishes, pots/pans, cookie sheets, casserole dishes, coffee makers (Keurig and regular), tea pot, blender, toaster, microwave, cutlery etc. I would suggest that you bring your own paper products (including paper plates, cups, bowls, cutlery, paper towels, also ziploc storage bags/containers if you are cooking and need to store leftovers). If you are traveling with children, bring your own plastic cups as there were no plastic cups-we forgot our cups at home. There were plenty of glass ones, but sometimes that can be tricky with little ones. The house did have basic cleaning products, so no need to bring any. The living room has a tv with basic cable access and dvd player and a fireplace (the owner provided duraflame logs-you cannot use any other firewood in the indoor fireplace per the owner's request). The basement level is unfinished and has a washer and dryer. Overall we really enjoyed our time at this property and would stay again. Only 'cons' were that we had to bring our own sheets & towels, but we knew in advance, so adjusted accordingly.
                                                                                                      • Submitted: Dec 30, 2016
                                                                                                      • Stayed: Dec 2016

                                                                                                      Excellent room and resort!

                                                                                                      5 of 5
                                                                                                      Very good! The only thing I wish was that there was an easier way to get to skip lift from bldg 26. Very icy
                                                                                                      • Submitted: Dec 29, 2016
                                                                                                      • Stayed: Dec 2016