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Stockbridge: Houses, Cottages & More (450+)

  • 1 - 50 of 450+
Additional fees apply. Taxes may be added.
    • 6 BR
    • 5 BA
    • 1 HF BA
    • Sleeps 16
    12
      • 3 BR
      • 3 BA
      • Sleeps 8
      20
        • 4 BR
        • 3 BA
        • 1 HF BA
        • Sleeps 12
        15
          • 4 BR
          • 3 BA
          • Sleeps 10
          13
            • 2 BR
            • 1 BA
            • Sleeps 6
            22
              • 3 BR
              • 2 BA
              • 1 HF BA
              • Sleeps 8
              7
                • Studio
                • 1 BA
                • Sleeps 2
                25
                  • 2 BR
                  • 1 BA
                  • Sleeps 6
                  6
                    • 3 BR
                    • 2 BA
                    • Sleeps 8
                    16
                      • 2 BR
                      • 2 BA
                      • Sleeps 6
                      6
                        • 6 BR
                        • 6 BA
                        • Sleeps 12
                        14
                          • 3 BR
                          • 3 BA
                          • Sleeps 10
                          12
                            • 3 BR
                            • 2 BA
                            • 1 HF BA
                            • Sleeps 8
                            3
                              • 2 BR
                              • 1 BA
                              • Sleeps 4
                              3
                                • 3 BR
                                • 2 BA
                                • Sleeps 5
                                16
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 8
                                  13
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 6
                                    9
                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 7
                                      7
                                        • 3 BR
                                        • 3 BA
                                        • Sleeps 6
                                        8
                                          • 4 BR
                                          • 1 BA
                                          • 1 HF BA
                                          • Sleeps 7
                                          10
                                            • 2 BR
                                            • 1 BA
                                            • 1 HF BA
                                            • Sleeps 6
                                            10
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 6
                                              9
                                                • 2 BR
                                                • 2 BA
                                                • 1 HF BA
                                                • Sleeps 6
                                                6
                                                  • 2 BR
                                                  • 1 BA
                                                  • Sleeps 6
                                                  2 Reviews
                                                    • 3 BR
                                                    • 1 BA
                                                    • 1 HF BA
                                                    • Sleeps 8
                                                    10
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      1 Review
                                                        • 4 BR
                                                        • 3 BA
                                                        • Sleeps 10
                                                        4
                                                          • 4 BR
                                                          • 2 BA
                                                          • 1 HF BA
                                                          • Sleeps 9
                                                          12
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 7
                                                            9
                                                              • 3 BR
                                                              • 2 BA
                                                              • 1 HF BA
                                                              • Sleeps 6
                                                              6
                                                                • 3 BR
                                                                • 3 BA
                                                                • Sleeps 5
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 6
                                                                    • 4 BR
                                                                    • 2 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 7
                                                                    1 Review
                                                                      • 7 BR
                                                                      • 4 BA
                                                                      • Sleeps 16
                                                                        • 7 BR
                                                                        • 5 BA
                                                                        • Sleeps 12
                                                                        1 Review
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                            • 5 BR
                                                                            • 5 BA
                                                                            • Sleeps 8
                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Sleeps 2
                                                                              11
                                                                                • 3 BR
                                                                                • 3 BA
                                                                                • Sleeps 6
                                                                                  • 2 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 6
                                                                                    2 Reviews
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 4
                                                                                        NEW!
                                                                                        • 5 BR
                                                                                        • 6 BA
                                                                                        • Sleeps 10
                                                                                          • 4 BR
                                                                                          • 3 BA
                                                                                          • Sleeps 6
                                                                                            • 3 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 5
                                                                                              • 4 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 8
                                                                                                • 4 BR
                                                                                                • 3 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 8
                                                                                                2 Reviews
                                                                                                  • 6 BR
                                                                                                  • 5 BA
                                                                                                  • Sleeps 16
                                                                                                  14
                                                                                                    NEW!
                                                                                                    • 6 BR
                                                                                                    • 5 BA
                                                                                                    • Sleeps 20
                                                                                                    7
                                                                                                    • 1 - 50 of 450+
                                                                                                     

                                                                                                    Recent Stockbridge Reviews

                                                                                                    Incredible place to stay

                                                                                                    5 of 5
                                                                                                    Some college friends and I spent a long weekend at the Playhouse. It was an incredible experience. The owner and property managers were both very responsive. It's still very new - I think we were only the 6th or 7th group to rent the place, so they're working out some minor kinks, but I have no doubt that they'll be resolved soon. There was no HDMI port accessible on either TV, but the owner has said he will get a port wired soon. Highly recommended!
                                                                                                    • Submitted: Sep 19, 2016
                                                                                                    • Stayed: Sep 2016

                                                                                                    Great Rental

                                                                                                    5 of 5
                                                                                                    The house was centrally located, internet, nice kitchen, comfortable bed (the one on the main floor), great shower, nice back yard, etc. Highly recommend.
                                                                                                    • Submitted: Sep 14, 2016
                                                                                                    • Stayed: Sep 2016

                                                                                                    peaceful Berkshires retreat

                                                                                                    5 of 5
                                                                                                    The Redway house is a beautiful and historic home situated in the woods between Stockbridge and West Stockbridge, both of which are an easy 5 minute drive away. We were looking for a last minute Labor Day escape from Manhattan with our two dogs. Luckily Redway House was available! The house had everything we needed for a comfortable stay -- including super comfy beds. We cooked on the grill out back the entire weekend and the house is stocked with most everything you need, including fresh herbs from the garden. Redway House was the peaceful retreat from the city that we were hoping for.
                                                                                                    • Submitted: Sep 9, 2016
                                                                                                    • Stayed: Sep 2016