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Canaan: Houses, Cottages & More (478)

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Additional fees apply. Taxes may be added.
    • 6 BR
    • 5 BA
    • 1 HF BA
    • Sleeps 16
    3
      • 5 BR
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      • Sleeps 12
      18
        • 3 BR
        • 2 BA
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        3
          • 3 BR
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          • 1 HF BA
          • Sleeps 10
          6
            • 4 BR
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            • Sleeps 12
            9
              • 4 BR
              • 4 BA
              • Sleeps 12
              3
                • 1 BR
                • 1 BA
                • Sleeps 2
                2 Reviews
                  • 6 BR
                  • 5 BA
                  • 1 HF BA
                  • Sleeps 13
                  6
                    • 3 BR
                    • 2 BA
                    • Sleeps 11
                    19
                      • 3 BR
                      • 2 BA
                      • Sleeps 9
                      3
                        • 3 BR
                        • 2 BA
                        • 1 HF BA
                        • Sleeps 8
                        1 Review
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                          • 1 BA
                          • Sleeps 4
                            • 3 BR
                            • 2 BA
                            • 1 HF BA
                            • Sleeps 8
                              • 3 BR
                              • 2 BA
                              • 1 HF BA
                              • Sleeps 9
                                • 4 BR
                                • 3 BA
                                • Sleeps 10
                                2 Reviews
                                  • 4 BR
                                  • 2 BA
                                  • 1 HF BA
                                  • Sleeps 7
                                  5
                                    • 5 BR
                                    • 3 BA
                                    • Sleeps 8
                                    2 Reviews
                                      • 2 BR
                                      • 1 BA
                                      • 1 HF BA
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                                      1 Review
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                                        • 1 BA
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                                        11
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                                            • 2 BR
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                                            3
                                              • 5 BR
                                              • 6 BA
                                              • Sleeps 10
                                                • 3 BR
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                                                • Sleeps 10
                                                  • 3 BR
                                                  • 2 BA
                                                  • 1 HF BA
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                                                  5
                                                    • 2 BR
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                                                      • 2 BA
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                                                      6
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                                                        3
                                                          • 4 BR
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                                                          • Sleeps 6
                                                            • 2 BR
                                                            • 1 BA
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                                                            1 Review
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 8
                                                              17
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 5
                                                                6
                                                                  • 2 BR
                                                                  • 2 BA
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                                                                  15
                                                                    • 3 BR
                                                                    • 4 BA
                                                                    • Sleeps 10
                                                                    3
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 11
                                                                      13
                                                                        • 5 BR
                                                                        • 4 BA
                                                                        • Sleeps 10
                                                                        2 Reviews
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                          1 Review
                                                                            • 3 BR
                                                                            • 3 BA
                                                                            • Sleeps 9
                                                                            4
                                                                              • 1 BR
                                                                              • 1 BA
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                                                                              6
                                                                                • 4 BR
                                                                                • 4 BA
                                                                                • Sleeps 10
                                                                                  • 5 BR
                                                                                  • 5 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 8
                                                                                  18
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 6
                                                                                    2 Reviews
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 7
                                                                                      9
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        3
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 7
                                                                                            • 5 BR
                                                                                            • 3 BA
                                                                                            • 2 HF BA
                                                                                            • Sleeps 12
                                                                                            3
                                                                                              • 3 BR
                                                                                              • 1 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 6
                                                                                              1 Review
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                1 Review
                                                                                                  • 3 BR
                                                                                                  • 3 BA
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                                                                                                    • 3 BR
                                                                                                    • 3 BA
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                                                                                                      • 6 BR
                                                                                                      • 5 BA
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                                                                                                      • Sleeps 10
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                                                                                                      • 1 - 50 of 478
                                                                                                       

                                                                                                      Recent Canaan Reviews

                                                                                                      Perfect vacation home in berkshires

                                                                                                      5 of 5
                                                                                                      This was our first trip to Berkshire and this beautiful property made it a perfect home for our family. Our kids didn't want to leave the house at all. It's so peaceful and quite. The pool was a treat for the kids. The house has an open floor plan that makes for a good setup for kids and grown ups to spread out and still enjoy together. It is conveniently located to all Berkshire attractions. The owners are a text away and were quick to respond to our questions. We couldn't have found a better place for our week away in the berkshires.
                                                                                                      • Submitted: Aug 15, 2016
                                                                                                      • Stayed: Jul 2016

                                                                                                      Nature Lover's Retreat

                                                                                                      5 of 5
                                                                                                      We are three professional women who rented here last week for 3 nights. The title fits this bucolic and spacious home perfectly. The decor is eclectic: the kitchen is intentionally stylish retro but with very modern appliances, including an espresso maker! The rest of the house is decorated in a playful, modern, and, most importantly, comfy style. Lots of cool appliances, including a modern record turntable with futuristic looking little speakers. AND a hot tub which we never got around to using. Large screen flat tv. We had breakfast on the back deck every morning overlooking the pretty backyard. We felt like we were hundreds of miles away from the fuss of the world, yet everywhere we wanted to go was within 15 minutes! Downtown Lenox was around 7 minutes away. We swam at the public beach at Stockbridge Bowl one day, and it was probably under 15 minutes away. We toured the Ventfort Mansion, which was about 8 minutes away. Stockbridge was around 15 minutes (if that) away. The owner responds immediately to any questions you send him. He left us a welcoming gift of a box of chocolates upon our arrival! Just one important piece of information: the Master Bedroom is private because it is at one end of the house and down a few stairs, and the other bedroom is up close to the other end; however, it does not have a door, which could inhibit a couple with small kids from getting romantic. I cannot imagine anyone being disappointed in this rental! Enjoy!
                                                                                                      • Submitted: Aug 10, 2016
                                                                                                      • Stayed: Aug 2016

                                                                                                      Beautiful retreat

                                                                                                      5 of 5
                                                                                                      We so enjoyed our weekend upstate at this beautifully maintained and decorated house. It was a perfect escape from the city with a lot to see and do within driving distance.
                                                                                                      • Submitted: Jul 31, 2016
                                                                                                      • Stayed: Jul 2016