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  • Showing 1-50 of 300+
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    Excellent! 4.5/5
    (6 reviews)
    avg/night
    • 3 BR
    • 2 BA
    • Sleeps 6
    House #640850vb
    6
    Viewed 5 times in the last 48 hours
      • 2 BR
      • 1 BA
      • Sleeps 4
      Apartment #3962367
      3
        • 3 BR
        • 1 BA
        • 1 HF BA
        • Sleeps 6
        Farmhouse #459350vb
        15
          Exceptional! 5.0/5
          (6 reviews)
          avg/night
          • 2 BR
          • 2 BA
          • Sleeps 6
          House #804956vb
          6
          Viewed 18 times in the last 48 hours
            Exceptional! 5.0/5
            (15 reviews)
            avg/night
            • 6 BR
            • 5 BA
            • Sleeps 20
            Estate #4258796
            15
            Viewed 103 times in the last 48 hours
              Wonderful! 4.9/5
              (9 reviews)
              avg/night
              • 3 BR
              • 2 BA
              • Sleeps 7
              House #330190
              9
              Viewed 5 times in the last 48 hours
                Exceptional! 5.0/5
                (45 reviews)
                avg/night
                • 1 BR
                • 2 BA
                • Sleeps 4
                Chalet #3022937
                45
                Viewed 37 times in the last 48 hours
                  Exceptional! 5.0/5
                  (80 reviews)
                  avg/night
                  • 2 BR
                  • 1 BA
                  • Sleeps 4
                  Cottage #216065
                  80
                  Viewed 82 times in the last 48 hours
                    Wonderful! 4.9/5
                    (20 reviews)
                    avg/night
                    • 2 BR
                    • 1 BA
                    • Sleeps 5
                    Cottage #707780vb
                    20
                    Viewed 19 times in the last 48 hours
                      Exceptional! 5.0/5
                      (30 reviews)
                      avg/night
                      • 3 BR
                      • 2 BA
                      • Sleeps 4
                      House #424508vb
                      30
                      Viewed 36 times in the last 48 hours
                        Wonderful! 4.9/5
                        (32 reviews)
                        avg/night
                        • 3 BR
                        • 3 BA
                        • Sleeps 8
                        House #406592vb
                        32
                        Viewed 25 times in the last 48 hours
                          Exceptional! 5.0/5
                          (53 reviews)
                          avg/night
                          • 4 BR
                          • 3 BA
                          • Sleeps 9
                          House #95599vb
                          53
                          Viewed 19 times in the last 48 hours
                            Exceptional! 5.0/5
                            (9 reviews)
                            avg/night
                            • 2 BR
                            • 2 BA
                            • Sleeps 6
                            Cottage #3790476
                            9
                            Viewed 19 times in the last 48 hours
                              Exceptional! 5.0/5
                              (7 reviews)
                              avg/night
                              • 5 BR
                              • 4 BA
                              • 1 HF BA
                              • Sleeps 12
                              Chateau / Country House #777079vb
                              7
                              Viewed 11 times in the last 48 hours
                                • 4 BR
                                • 2 BA
                                • Sleeps 8
                                House #711169vb
                                3
                                Viewed 26 times in the last 48 hours
                                  Wonderful! 4.9/5
                                  (23 reviews)
                                  avg/night
                                  • 5 BR
                                  • 5 BA
                                  • Sleeps 12
                                  House #729783vb
                                  23
                                  Viewed 18 times in the last 48 hours
                                    Excellent! 4.7/5
                                    (7 reviews)
                                    avg/night
                                    • 4 BR
                                    • 3 BA
                                    • Sleeps 8
                                    Farmhouse #3765427
                                    7
                                    Viewed 8 times in the last 48 hours
                                      Wonderful! 4.8/5
                                      (18 reviews)
                                      avg/night
                                      • 3 BR
                                      • 3 BA
                                      • 1 HF BA
                                      • Sleeps 10
                                      House #272149vb
                                      18
                                      Viewed 23 times in the last 48 hours
                                        Exceptional! 5.0/5
                                        (14 reviews)
                                        avg/night
                                        • 5 BR
                                        • 2 BA
                                        • 1 HF BA
                                        • Sleeps 10
                                        Barn #616214vb
                                        14
                                        Viewed 23 times in the last 48 hours
                                          Exceptional! 5.0/5
                                          (48 reviews)
                                          avg/night
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 2
                                          Apartment #675472vb
                                          48
                                          Viewed 39 times in the last 48 hours
                                            Exceptional! 5.0/5
                                            (17 reviews)
                                            avg/night
                                            • 6 BR
                                            • 4 BA
                                            • 1 HF BA
                                            • Sleeps 12
                                            Estate #629154vb
                                            17
                                            Viewed 8 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (15 reviews)
                                              avg/night
                                              • 5 BR
                                              • 4 BA
                                              • 1 HF BA
                                              • Sleeps 15
                                              House #867170vb
                                              15
                                              Viewed 45 times in the last 48 hours
                                                Excellent! 4.7/5
                                                (25 reviews)
                                                avg/night
                                                • 3 BR
                                                • 1 BA
                                                • 1 HF BA
                                                • Sleeps 6
                                                House #178378
                                                25
                                                Viewed 18 times in the last 48 hours
                                                  Exceptional! 5.0/5
                                                  (22 reviews)
                                                  avg/night
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 5
                                                  Cottage #165627vb
                                                  22
                                                  Viewed 32 times in the last 48 hours
                                                    Wonderful! 4.9/5
                                                    (38 reviews)
                                                    avg/night
                                                    • 6 BR
                                                    • 5 BA
                                                    • Sleeps 14
                                                    House #470802vb
                                                    38
                                                    Viewed 95 times in the last 48 hours
                                                      Exceptional! 5.0/5
                                                      (8 reviews)
                                                      avg/night
                                                      • 7 BR
                                                      • 4 BA
                                                      • Sleeps 24
                                                      Lodge #3967190
                                                      8
                                                      Viewed 84 times in the last 48 hours
                                                        Wonderful! 4.9/5
                                                        (13 reviews)
                                                        $89
                                                        avg/night
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 3
                                                        Cottage #555172vb
                                                        13
                                                        Viewed 6 times in the last 48 hours
                                                          Wonderful! 4.8/5
                                                          (12 reviews)
                                                          avg/night
                                                          • 4 BR
                                                          • 2 BA
                                                          • 1 HF BA
                                                          • Sleeps 12
                                                          House #3934989
                                                          12
                                                          Viewed 67 times in the last 48 hours
                                                            Wonderful! 4.9/5
                                                            (34 reviews)
                                                            avg/night
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 2
                                                            Apartment #3591655
                                                            34
                                                            Viewed 22 times in the last 48 hours
                                                              Wonderful! 4.9/5
                                                              (17 reviews)
                                                              avg/night
                                                              • 5 BR
                                                              • 2 BA
                                                              • 1 HF BA
                                                              • Sleeps 12
                                                              House #561543vb
                                                              17
                                                              Viewed 7 times in the last 48 hours
                                                                Wonderful! 4.8/5
                                                                (9 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 5
                                                                Farmhouse #719766vb
                                                                9
                                                                Viewed 13 times in the last 48 hours
                                                                  Exceptional! 5.0/5
                                                                  (10 reviews)
                                                                  avg/night
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 8
                                                                  House #4193492
                                                                  10
                                                                  Viewed 7 times in the last 48 hours
                                                                    Wonderful! 4.8/5
                                                                    (30 reviews)
                                                                    avg/night
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 5
                                                                    House #100686
                                                                    30
                                                                    Viewed 19 times in the last 48 hours
                                                                      Exceptional! 5.0/5
                                                                      (16 reviews)
                                                                      avg/night
                                                                      • 4 BR
                                                                      • 3 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 12
                                                                      House #583082vb
                                                                      16
                                                                      Viewed 32 times in the last 48 hours
                                                                        avg/night
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 6
                                                                        Apartment #630322vb
                                                                        4
                                                                        Viewed 10 times in the last 48 hours
                                                                          avg/night
                                                                          • 4 BR
                                                                          • 2 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 8
                                                                          House #4222851
                                                                          Viewed 8 times in the last 48 hours
                                                                            Wonderful! 4.8/5
                                                                            (25 reviews)
                                                                            avg/night
                                                                            • 3 BR
                                                                            • 1 BA
                                                                            • Sleeps 6
                                                                            House #3002193
                                                                            25
                                                                            Viewed 11 times in the last 48 hours
                                                                              Wonderful! 4.9/5
                                                                              (16 reviews)
                                                                              avg/night
                                                                              • 6 BR
                                                                              • 5 BA
                                                                              • Sleeps 12
                                                                              House #406384vb
                                                                              16
                                                                              Viewed 37 times in the last 48 hours
                                                                                Wonderful! 4.9/5
                                                                                (32 reviews)
                                                                                avg/night
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 3
                                                                                House #135474vb
                                                                                32
                                                                                Viewed 10 times in the last 48 hours
                                                                                  Wonderful! 4.9/5
                                                                                  (16 reviews)
                                                                                  avg/night
                                                                                  • 6 BR
                                                                                  • 6 BA
                                                                                  • Sleeps 12
                                                                                  Estate #568397vb
                                                                                  16
                                                                                  Viewed 45 times in the last 48 hours
                                                                                    Wonderful! 4.8/5
                                                                                    (6 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                    Cottage #3953792
                                                                                    6
                                                                                    Viewed 28 times in the last 48 hours
                                                                                      Wonderful! 4.9/5
                                                                                      (15 reviews)
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 4
                                                                                      Apartment #571935vb
                                                                                      15
                                                                                      Viewed 22 times in the last 48 hours
                                                                                        Exceptional! 5.0/5
                                                                                        (16 reviews)
                                                                                        avg/night
                                                                                        • 6 BR
                                                                                        • 5 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 16
                                                                                        House #396147vb
                                                                                        16
                                                                                        Viewed 30 times in the last 48 hours
                                                                                          Wonderful! 4.8/5
                                                                                          (5 reviews)
                                                                                          avg/night
                                                                                          • 5 BR
                                                                                          • 3 BA
                                                                                          • Sleeps 10
                                                                                          House #4148450
                                                                                          5
                                                                                          Viewed 39 times in the last 48 hours
                                                                                            Exceptional! 5.0/5
                                                                                            (20 reviews)
                                                                                            avg/night
                                                                                            • 3 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 8
                                                                                            House #224680
                                                                                            20
                                                                                            Viewed 38 times in the last 48 hours
                                                                                              Exceptional! 5.0/5
                                                                                              (14 reviews)
                                                                                              avg/night
                                                                                              • 4 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 9
                                                                                              Estate #4067367
                                                                                              14
                                                                                              Viewed 30 times in the last 48 hours
                                                                                                Wonderful! 4.8/5
                                                                                                (28 reviews)
                                                                                                avg/night
                                                                                                • 5 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 12
                                                                                                House #424518vb
                                                                                                28
                                                                                                Viewed 32 times in the last 48 hours
                                                                                                  Wonderful! 4.9/5
                                                                                                  (9 reviews)
                                                                                                  avg/night
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 3
                                                                                                  Apartment #606558vb
                                                                                                  9
                                                                                                  Viewed 17 times in the last 48 hours
                                                                                                    Exceptional! 5.0/5
                                                                                                    (9 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 8
                                                                                                    House #640319vb
                                                                                                    9
                                                                                                    Viewed 39 times in the last 48 hours
                                                                                                      Exceptional! 5.0/5
                                                                                                      (5 reviews)
                                                                                                      avg/night
                                                                                                      • 5 BR
                                                                                                      • 3 BA
                                                                                                      • Sleeps 10
                                                                                                      Lodge #487322vb
                                                                                                      5
                                                                                                      Viewed 5 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Hillsdale: Vacation Rentals (537)

                                                                                                       

                                                                                                      Recent Hillsdale Reviews

                                                                                                      Stunning- perfect group getaway!

                                                                                                      5 of 5
                                                                                                      Me & my husband came here for our weekend wedding celebration with our family & friends. This house has EVERYTHING you need to enjoy yourself. We had enough space for 20 people (including kids and even our pup!) to sleep and play with more than enough room. It goes without saying that the architecture is stunning (It looks even better in person than the photos!) The property manager was attentive to our needs if anything came up, without intruding on our privacy. They even left out a dog bed & water bowl for our pup! The downstairs was a great playroom with the tv and table tennis. They had already set up the airbeds for us for the extra guests sleeping in the yoga studio! It was the perfect weekend that we'll remember for ever! Just a couple things to note: the hot tub was at the house but elsewhere on the property (it might say this in the listing, so maybe we just didn't read correctly) and the fireplace is downstairs (and currently not working, which would have been nice to have a heads up on.) otherwise, this house far surpassed our expectations. The property its on is quiet & serene.
                                                                                                      • Submitted: Jan 20, 2017
                                                                                                      • Stayed: Jan 2017

                                                                                                      Perfect getaway!

                                                                                                      5 of 5
                                                                                                      Our group of 6 adults and 1 infant enjoyed our time at the Grey House over MLK weekend. The house is perfectly located, just 2.5 hours from NYC and Boston, for us to meet. Ed has decorated the place with beautiful furniture and art work from their travels in Europe. There are many houses in the area for rent, but the Grey House is just perfect for us with the decor, layout, and comfort. The house is also stocked with everything we needed including a fully functional kitchen, many extra towels, and sheets. Our group made use the kitchen and big dinning table for many lunches and dinners. Thank you for opening the house to us and we highly recommend the fabulous Grey House for your next Berkshire/Hudson Valley trip.
                                                                                                      • Submitted: Jan 17, 2017
                                                                                                      • Stayed: Jan 2017

                                                                                                      Nice cottage 10 min from GB

                                                                                                      5 of 5
                                                                                                      Stayed with family for a weekend of skiing at Butternut. Plenty of room for us to spread out and relax. Front porch great area to stow the ski stuff. Short drive to the mountain and plenty close to all the restaurants in town. Would definitely stay again.
                                                                                                      • Submitted: Jan 7, 2017
                                                                                                      • Stayed: Dec 2016