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Hillsdale: Houses, Cottages & More (545)

  • 1 - 30 of 545
    • 3 BR
    • 2 BA
    • Sleeps 8
    21
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        • 4 BR
        • 3 BA
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        1 Review
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          • 4 BR
          • 3 BA
          • Sleeps 8
          4
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            • 3 BR
            • 1 BA
            • Sleeps 6
            12
              • 1 BR
              • 1 BA
              • Sleeps 3
              5
                • 3 BR
                • Sleeps 13
                28
                  • 3 BR
                  • 4 BA
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                    • 3 BR
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                    5
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                      • 2 BR
                      • 1 BA
                      • Sleeps 7
                      13
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                        • 1 BR
                        • 1 BA
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                          • 3 BR
                          • 1 BA
                          • 1 HF BA
                          • Sleeps 6
                          15
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                            $103
                            avg/night
                            • 1 BR
                            • 1 BA
                            • Sleeps 3
                            10
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                              • 3 BR
                              • 2 BA
                              • 1 HF BA
                              • Sleeps 10
                              7
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                                • 3 BR
                                • 2 BA
                                • Sleeps 8
                                1 Review
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                                  • 3 BR
                                  • 3 BA
                                  • Sleeps 10
                                  2 Reviews
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                                    • 3 BR
                                    • 3 BA
                                    • Sleeps 8
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                                      • 6 BR
                                      • 5 BA
                                      • Sleeps 10
                                      2 Reviews
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                                        • 4 BR
                                        • 3 BA
                                        • Sleeps 8
                                        3
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                                          • 5 BR
                                          • 4 BA
                                          • 1 HF BA
                                          • Sleeps 10
                                          18
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                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 4
                                            13
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                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 4
                                              3
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                                                • 3 BR
                                                • 2 BA
                                                • 1 HF BA
                                                • Sleeps 9
                                                3
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                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 8
                                                  33
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                                                    • 3 BR
                                                    • 3 BA
                                                    • Sleeps 8
                                                    2 Reviews
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                                                      • 4 BR
                                                      • 2 BA
                                                      • Sleeps 11
                                                      5
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                                                        • 4 BR
                                                        • 5 BA
                                                        • Sleeps 8
                                                        4
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                                                          • 3 BR
                                                          • 2 BA
                                                          • 1 HF BA
                                                          • Sleeps 8
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                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 8
                                                            Request to Book View Details
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                                                              • 2 BR
                                                              • 1 BA
                                                              • Sleeps 4
                                                              3
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                                                              • 1 - 30 of 545
                                                               

                                                              Recent Hillsdale Reviews

                                                              Wonderful Weekend Retreat

                                                              5 of 5
                                                              We had 3 generations get together for a very relaxing time at this gorgeous house.The property is on a beautiful setting far away from other houses with a view of the large pond across the street.The house is fully equipped and impeccably decorated.We especially enjoyed the fully windowed dining room,the connected family room and modern kitchen, and the walk-in shower in the master bedroom.The entire house was inviting and the kids liked hanging out in the downstairs playroom.We definitely will return
                                                              • Submitted: May 2, 2016
                                                              • Stayed: Apr 2016

                                                              Highly Recommended!

                                                              5 of 5
                                                              We stayed here with a group of friends over the weekend. The house is great, large, and clean. There are a lot of activities that you can enjoy during the stay such as badminton, volleyball, soccer and kayak. We love the deck that the house offers; a perfect view for an early morning coffee and BBQ. The kitchen is fully equipped and the basement have a lot of lifeguard jackets (all sizes) and many sports gear and equipment. There are 2 charcoal grills, a television (but DVD and VHS only), no Wifi, no signals with T-Mobile phone there (not sure about other carriers.) We were very sad that our short trip has come to an end. Thanks William for being such an awesome host. He is very helpful, nice and friendly. If we had any questions he always responds to our message quite quickly. We would love to stay here again. Highly recommended!
                                                              • Submitted: Mar 28, 2016
                                                              • Stayed: Mar 2016

                                                              Orchard House

                                                              5 of 5
                                                              We had a very relaxing winter break in Hillsdale at the Orchard House. It's very comfortable and quiet and you are indeed on the grounds of a horse farm and usually see a couple of horses grazing when you look out the front window. The kitchen is big and has a solid set of the basics for cooking meals, and there are some great stores in the area for food, and we were close to restaurants in Hillsdale and Great Barrington when we didn't feel like cooking. Sadly there wasn't much snow during our trip so my son and I spent a fair amount of time on the foosball table in the basement, which was a lot of fun as was building fires in the wood stove.
                                                              • Submitted: Jan 6, 2016
                                                              • Stayed: Dec 2015