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Canaan: Vacation Rental Estates (20)

  • 1 - 20 of 20
Additional fees apply. Taxes may be added.
    • 6 BR
    • 5 BA
    • 1 HF BA
    • Sleeps 13
    6
      • 2 BR
      • 1 BA
      • Sleeps 6
      1 Review
        • 4 BR
        • 4 BA
        • Sleeps 10
        2 Reviews
          • 6 BR
          • 5 BA
          • Sleeps 20
          7
            • 6 BR
            • 5 BA
            • Sleeps 10
            12
              • 3 BR
              • 5 BA
              • Sleeps 10
                • 5 BR
                • 6 BA
                • Sleeps 10
                  • 10 BR
                  • 9 BA
                  • 1 HF BA
                  • Sleeps 17
                    • 5 BR
                    • 5 BA
                    • 1 HF BA
                    • Sleeps 10
                    1 Review
                      • 7 BR
                      • 4 BA
                      • Sleeps 16
                        • 8 BR
                        • 4 BA
                        • 2 HF BA
                        • Sleeps 17
                        14
                          • 9 BR
                          • 8 BA
                          • Sleeps 16
                          5
                            • 3 BR
                            • 3 BA
                            • Sleeps 6
                            2 Reviews
                              • 5 BR
                              • 4 BA
                              • 2 HF BA
                              • Sleeps 10
                              3
                                • 5 BR
                                • 2 BA
                                • Sleeps 10
                                  View details for price
                                  • 7 BR
                                  • 7 BA
                                  • 1 HF BA
                                  • Sleeps 14
                                  7
                                    • 7 BR
                                    • 9 BA
                                    • 1 HF BA
                                    • Sleeps 14
                                    8
                                      • 7 BR
                                      • 7 BA
                                      • 1 HF BA
                                      • Sleeps 14
                                      8
                                        • 8 BR
                                        • 4 BA
                                        • 1 HF BA
                                        • Sleeps 18
                                        4
                                          • 8 BR
                                          • 4 BA
                                          • 2 HF BA
                                          • Sleeps 20
                                          1 Review
                                          • 1 - 20 of 20
                                           

                                          Recent Canaan 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

                                          Making memories happens here.

                                          5 of 5
                                          This is the absolute perfect home for a family gathering. My two children, their spouses and a total of 6 children ranging in age from 3 to 11, along with us, the grandparents, spent a delightful week enjoying the wonderful swimming pond, the adorable tree house and the tennis courts. We explored the area on two of the mornings, riding on the Harlem Rail Trail and taking an easy hike to Bash Bish Falls. The furnishings are very tastefully done but not ostentatious. Don't be afraid to bring kids here -it is made for them, complete with a playroom (perfect for legos) downstairs. We each had our own space at night, making it easy to put little ones to bed. The Whites are lovely people. They were more than accommodating and were perfect hosts. We enjoyed meeting them two weeks before we stayed at their beautiful home and they were so welcoming. We had a few more people drop in the last Saturday we were there and were able to find food, drinks, etc. right in Chatham, about 7 miles away. So very convenient. There are also little shops and restaurants and delis that are very interesting to explore. I would highly recommend this property to friends and relatives. The ammenities keep young and old alike very happy. You will not be disappointed!
                                          • Submitted: Jun 30, 2015
                                          • Stayed: Jun 2015

                                          Luxurious Rockefeller-like New England mansion

                                          5 of 5
                                          I travel extensively throughout the world for my work and have stayed at many of the worlds great hotels. Quite frankly, I was not expecting but was pleasantly surprised to discover a world class property in the tiny town of Lenox. The Winthrop Estate is a perfect marriage of an historical Rockefeller-like New England mansion of the 1920s and a Four Seasons hotel of today. This is how we’d describe our stay at Winthrop Estate. The experience was nothing short of going back a hundred years to the days when The Berkshires were a pastoral retreat for the great Industrialists and statesmen of the day while enjoying the luxury of the current era. The Winthrop Estate is neatly tucked away, thus we experienced as little or as much of civilization as we desired. In the morning we took a walk to the center of Lenox (a sleepy but adorable typical New England town), which is just a five minutes away. We stopped at a bagel shop, then got coffee at a French patisserie, and then just walked and enjoyed the tranquility and simple beauty of this historic area. The Winthrop Estate was a perfect place to decompress from the busyness of everyday life. We really enjoyed our stay and highly recommend this treasure to everyone.
                                          • Submitted: Jun 14, 2015
                                          • Stayed: Nov 2014