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Hillsdale: Houses, Cottages & More (714)

  • 1 - 30 of 714
    • 3 BR
    • 2 BA
    • Sleeps 8
    21
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      • 2 BR
      • 1 BA
      • Sleeps 4
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        • 4 BR
        • 3 BA
        • Sleeps 10
        1 Review
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          • 3 BR
          • 1 BA
          • Sleeps 6
          12
            • 3 BR
            • Sleeps 13
            28
              • 4 BR
              • 3 BA
              • Sleeps 8
              4
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                • 1 BR
                • 1 BA
                • Sleeps 3
                5
                  • 3 BR
                  • 2 BA
                  • Sleeps 6
                  5
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                    • 3 BR
                    • 4 BA
                    • Sleeps 6
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                      • 2 BR
                      • 1 BA
                      • Sleeps 7
                      13
                        • 3 BR
                        • 1 BA
                        • 1 HF BA
                        • Sleeps 6
                        15
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                          • 2 BR
                          • 2 BA
                          • 1 HF BA
                          • Sleeps 5
                          17
                            • 1 BR
                            • 1 BA
                            • Sleeps 4
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                              • 2 BR
                              • 1 BA
                              • Sleeps 4
                              8
                                $105
                                avg/night
                                • 1 BR
                                • 1 BA
                                • Sleeps 3
                                9
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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
                                                11
                                                  • 5 BR
                                                  • 2 BA
                                                  • 1 HF BA
                                                  • Sleeps 14
                                                  6
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                                                    • 3 BR
                                                    • 3 BA
                                                    • 1 HF BA
                                                    • Sleeps 8
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 4
                                                      2 Reviews
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                                                        • 3 BR
                                                        • 2 BA
                                                        • 1 HF BA
                                                        • Sleeps 9
                                                        2 Reviews
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                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 8
                                                          33
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                                                            • 5 BR
                                                            • 4 BA
                                                            • 1 HF BA
                                                            • Sleeps 12
                                                            3
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                                                              • 3 BR
                                                              • 3 BA
                                                              • Sleeps 8
                                                              2 Reviews
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                                                              • 1 - 30 of 714
                                                               

                                                              Recent Hillsdale Reviews

                                                              Great place for skiing family

                                                              5 of 5
                                                              We were a family of 3 spending a skiing weekend along with our 14 year old daughter's 2 friends. We have rented a number of VRBO's the past couple of years and have never been disappointed, but this property was certainly the nicest one we have stayed in. Beautifully renovated kitchen and master bath, nice wood floors, and gas fireplace being the highlights for us. The owners were very responsive regarding one minor issue (reboot of the internet modem required), and the caretaker who lives on the property next door addressed it while we were at dinner. Having a built-in pool and proximity to the lake would suggest this would be good summer property as well.
                                                              • Submitted: Apr 3, 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

                                                              Beautiful, clean and spacious home!

                                                              5 of 5
                                                              What a great home. My family and I just had the opportunity to rent this house during our three day Christmas weekend. The house is a perfect size for one or two families. It has everything you can think of, extra blankets, sheets, towels, etc. There were 5 bikes lined up when you enter the house. There was also an air hockey machine my entire family had a lot of fun with that. There is a nice spacious deck on the second floor, great for bbq's or just to hang out during the warm weather. I would truly recommend this house to anyone looking to relax and enjoy your home away from home. Also, the owners Bill and Eileen were great. Very quick and responsive to all of my emails. They left us a big box of chocolate. I think that's just a wonderful way for them to welcome us.
                                                              • Submitted: Dec 30, 2015
                                                              • Stayed: Dec 2015