check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Cheshire: Houses, Condos & More (300+)

  • 1 - 50 of 300+
Additional fees apply. Taxes may be added.
    Excellent! 4.6/5
    (16 reviews)
    avg/night
    • 2 BR
    • 1 BA
    • Sleeps 5
    House #122780
    16
    Viewed 14 times in the last 48 hours
      Excellent! 4.7/5
      (21 reviews)
      avg/night
      • 4 BR
      • 1 BA
      • Sleeps 10
      Barn #346642vb
      21
      Viewed 15 times in the last 48 hours
        Wonderful! 4.9/5
        (17 reviews)
        avg/night
        • 2 BR
        • 1 BA
        • Sleeps 6
        Cottage #300900
        17
        Viewed 21 times in the last 48 hours
          Wonderful! 4.8/5
          (23 reviews)
          avg/night
          • 2 BR
          • 2 BA
          • Sleeps 6
          Condo #238631vb
          23
            Excellent! 4.7/5
            (9 reviews)
            avg/night
            • 3 BR
            • 1 BA
            • 1 HF BA
            • Sleeps 6
            Chateau / Country House #4149878
            9
            Viewed 12 times in the last 48 hours
              Wonderful! 4.8/5
              (13 reviews)
              avg/night
              • 5 BR
              • 3 BA
              • Sleeps 10
              House #603552vb
              13
              Viewed 30 times in the last 48 hours
                • 2 BR
                • 2 BA
                • Sleeps 8
                Condo #724286vb
                1
                Viewed 28 times in the last 48 hours
                  avg/night
                  • 7 BR
                  • 3 BA
                  • 1 HF BA
                  • Sleeps 14
                  House #4223261
                  2
                  Viewed 36 times in the last 48 hours
                    avg/night
                    • 2 BR
                    • 2 BA
                    • Sleeps 8
                    Condo #907348vb
                    Viewed 21 times in the last 48 hours
                      avg/night
                      • 2 BR
                      • 2 BA
                      • Sleeps 8
                      Condo #4281302
                      Viewed 14 times in the last 48 hours
                        Wonderful! 4.9/5
                        (36 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Sleeps 10
                        House #274704vb
                        36
                        Viewed 27 times in the last 48 hours
                          • 5 BR
                          • 2 BA
                          • 1 HF BA
                          • Sleeps 9
                          House #923513vb
                          1
                          Viewed 16 times in the last 48 hours
                            Exceptional! 5.0/5
                            (25 reviews)
                            avg/night
                            • 2 BR
                            • 2 BA
                            • Sleeps 6
                            Condo #651723vb
                            25
                            Viewed 15 times in the last 48 hours
                              avg/night
                              • 6 BR
                              • 3 BA
                              • 1 HF BA
                              • Sleeps 17
                              House #937764
                              10
                              Viewed 30 times in the last 48 hours
                                Exceptional! 5.0/5
                                (46 reviews)
                                avg/night
                                • 3 BR
                                • 2 BA
                                • Sleeps 8
                                Condo #575909vb
                                46
                                Viewed 25 times in the last 48 hours
                                  Exceptional! 5.0/5
                                  (10 reviews)
                                  avg/night
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 6
                                  Condo #786429vb
                                  10
                                  Viewed 9 times in the last 48 hours
                                    • 2 BR
                                    • 2 BA
                                    • Sleeps 8
                                    Condo #3815326
                                    Viewed 15 times in the last 48 hours
                                      avg/night
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 8
                                      Condo #650023vb
                                      Viewed 9 times in the last 48 hours
                                        Wonderful! 4.9/5
                                        (11 reviews)
                                        avg/night
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 4
                                        Apartment #129461vb
                                        11
                                        Viewed 10 times in the last 48 hours
                                          Exceptional! 5.0/5
                                          (6 reviews)
                                          avg/night
                                          • 4 BR
                                          • Sleeps 10
                                          Condo #101805
                                          6
                                          Viewed 17 times in the last 48 hours
                                            • 1 BR
                                            • 1 BA
                                            • Sleeps 4
                                            Condo #664124vb
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 4
                                              Condo #663246vb
                                                Exceptional! 5.0/5
                                                (7 reviews)
                                                avg/night
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 8
                                                Condo #105168
                                                7
                                                Viewed 10 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 8 times in the last 48 hours
                                                    Wonderful! 4.9/5
                                                    (22 reviews)
                                                    avg/night
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 6
                                                    House #3011344
                                                    22
                                                    Viewed 10 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 9 times in the last 48 hours
                                                        Wonderful! 4.9/5
                                                        (7 reviews)
                                                        avg/night
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        House #3836464
                                                        7
                                                        Viewed 52 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 12 times in the last 48 hours
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 8
                                                            Condo #620198vb
                                                              Wonderful! 4.9/5
                                                              (22 reviews)
                                                              avg/night
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 4
                                                              House #310035vb
                                                              22
                                                              Viewed 18 times in the last 48 hours
                                                                Wonderful! 4.8/5
                                                                (13 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                Cottage #962761
                                                                13
                                                                Viewed 8 times in the last 48 hours
                                                                  avg/night
                                                                  • 3 BR
                                                                  • 1 BA
                                                                  • Sleeps 6
                                                                  Apartment #901029vb
                                                                  1
                                                                  Viewed 6 times in the last 48 hours
                                                                    Wonderful! 4.8/5
                                                                    (22 reviews)
                                                                    avg/night
                                                                    • 7 BR
                                                                    • 3 BA
                                                                    • Sleeps 18
                                                                    House #251195vb
                                                                    22
                                                                    Viewed 48 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 17 times in the last 48 hours
                                                                        Excellent! 4.4/5
                                                                        (10 reviews)
                                                                        avg/night
                                                                        • 2 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                        Cabin #395895
                                                                        10
                                                                        Viewed 5 times in the last 48 hours
                                                                          Excellent! 4.4/5
                                                                          (11 reviews)
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 4
                                                                          House #3860654
                                                                          11
                                                                          Viewed 14 times in the last 48 hours
                                                                            Wonderful! 4.9/5
                                                                            (33 reviews)
                                                                            avg/night
                                                                            • 3 BR
                                                                            • 1 BA
                                                                            • Sleeps 8
                                                                            House #469617vb
                                                                            33
                                                                            Viewed 13 times in the last 48 hours
                                                                              Exceptional! 5.0/5
                                                                              (10 reviews)
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              House #471229vb
                                                                              10
                                                                              Viewed 16 times in the last 48 hours
                                                                                • 5 BR
                                                                                • 3 BA
                                                                                • 2 HF BA
                                                                                • Sleeps 9
                                                                                Estate #802737vb
                                                                                  Exceptional! 5.0/5
                                                                                  (26 reviews)
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 5
                                                                                  Farmhouse #228968
                                                                                  26
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 1 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 6
                                                                                    House #4284743
                                                                                    1
                                                                                    Viewed 14 times in the last 48 hours
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 10
                                                                                      Estate #3911459
                                                                                      3
                                                                                      Viewed 9 times in the last 48 hours
                                                                                        avg/night
                                                                                        • 3 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 8
                                                                                        Condo #878199vb
                                                                                        1
                                                                                        Viewed 9 times in the last 48 hours
                                                                                          Wonderful! 4.8/5
                                                                                          (13 reviews)
                                                                                          avg/night
                                                                                          • 4 BR
                                                                                          • 3 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 12
                                                                                          House #3465249
                                                                                          13
                                                                                          Viewed 7 times in the last 48 hours
                                                                                            avg/night
                                                                                            • 3 BR
                                                                                            • 1 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 6
                                                                                            House #4272947
                                                                                            1
                                                                                            Viewed 20 times in the last 48 hours
                                                                                              • 5 BR
                                                                                              • 5 BA
                                                                                              • Sleeps 12
                                                                                              House #4018856
                                                                                              1
                                                                                              Viewed 28 times in the last 48 hours
                                                                                                Wonderful! 4.8/5
                                                                                                (22 reviews)
                                                                                                avg/night
                                                                                                • 7 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 10
                                                                                                Farmhouse #444851vb
                                                                                                22
                                                                                                Viewed 30 times in the last 48 hours
                                                                                                  Excellent! 4.6/5
                                                                                                  (14 reviews)
                                                                                                  avg/night
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  Apartment #133082
                                                                                                  14
                                                                                                  Viewed 7 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (9 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • 1 HF BA
                                                                                                    • Sleeps 9
                                                                                                    Condo #595232vb
                                                                                                    9
                                                                                                    Viewed 11 times in the last 48 hours
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 7
                                                                                                      House #286733vb
                                                                                                      9
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Cheshire Reviews

                                                                                                      Excellent retreat for a family thanksgiving!

                                                                                                      5 of 5
                                                                                                      We had a younger generation thanksgiving get together at the Rose and Goat retreat, and it was absolutely perfect! The location was great, a short hop to North Adams and about 30 minutes to Williamstown, and the views from the house are spectacular. Margo was incredibly helpful in planning our getaway, and was a kind and generous host. We are looking forward to returning to Rose and Goat!
                                                                                                      • Submitted: Nov 30, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Thanksgiving

                                                                                                      5 of 5
                                                                                                      What a delight to arrive at the house to find 6 inches of fresh snow! My grandson and I made a snow man while the fire cracked away in the fire pit. We all loved the house and the kitchen is amazing! After we all hiked in the cold and the snow, my entire family enjoyed a quick warm up thanks to the radiant heat tiles in the kitchen. My three little ones also loved the Roman style bathtub. The owner is a great guy and responds quickly to emails, texts, of calls. We can't wait to return. One of our best holidays!
                                                                                                      • Submitted: Nov 27, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      We stayed at this lovely Williamstown house during homecoming weekend

                                                                                                      5 of 5
                                                                                                      The house is great and Ashley the alum/owner/manager is terrific too. Very comfortable and big enough to hold a party for the football team.
                                                                                                      • Submitted: Nov 17, 2016
                                                                                                      • Stayed: Nov 2016