check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit
  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
  View map Map
    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
      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
        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
          (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
                • 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
                    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
                      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
                          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
                            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
                              (17 reviews)
                              avg/night
                              • 5 BR
                              • 2 BA
                              • 1 HF BA
                              • Sleeps 12
                              House #561543vb
                              17
                              Viewed 7 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
                                      • 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
                                              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
                                                    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
                                                      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
                                                        Wonderful! 4.9/5
                                                        (11 reviews)
                                                        avg/night
                                                        • 4 BR
                                                        • 2 BA
                                                        • Sleeps 10
                                                        House #830745vb
                                                        11
                                                        Viewed 10 times in the last 48 hours
                                                          Exceptional! 5.0/5
                                                          (8 reviews)
                                                          avg/night
                                                          • 2 BR
                                                          • 3 BA
                                                          • Sleeps 6
                                                          House #4226428
                                                          8
                                                            Wonderful! 4.9/5
                                                            (10 reviews)
                                                            avg/night
                                                            • 4 BR
                                                            • 4 BA
                                                            • 1 HF BA
                                                            • Sleeps 12
                                                            House #4050256
                                                            10
                                                            Viewed 20 times in the last 48 hours
                                                              Exceptional! 5.0/5
                                                              (15 reviews)
                                                              avg/night
                                                              • 4 BR
                                                              • 2 BA
                                                              • Sleeps 8
                                                              House #592104vb
                                                              15
                                                              Viewed 18 times in the last 48 hours
                                                                Exceptional! 5.0/5
                                                                (16 reviews)
                                                                avg/night
                                                                • 4 BR
                                                                • 3 BA
                                                                • Sleeps 10
                                                                House #251535vb
                                                                16
                                                                Viewed 11 times in the last 48 hours
                                                                  Excellent! 4.7/5
                                                                  (27 reviews)
                                                                  avg/night
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 8
                                                                  House #419897vb
                                                                  27
                                                                  Viewed 40 times in the last 48 hours
                                                                    Exceptional! 5.0/5
                                                                    (9 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 8
                                                                    House #854910vb
                                                                    9
                                                                    Viewed 12 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (19 reviews)
                                                                      avg/night
                                                                      • 5 BR
                                                                      • 3 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 15
                                                                      House #660967vb
                                                                      19
                                                                      Viewed 34 times in the last 48 hours
                                                                        Exceptional! 5.0/5
                                                                        (8 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 6
                                                                        House #4153058
                                                                        8
                                                                        Viewed 8 times in the last 48 hours
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 8
                                                                          House #570547vb
                                                                          3
                                                                            Exceptional! 5.0/5
                                                                            (7 reviews)
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 8
                                                                            House #585864vb
                                                                            7
                                                                            Viewed 21 times in the last 48 hours
                                                                              Wonderful! 4.8/5
                                                                              (16 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 10
                                                                              House #601571vb
                                                                              16
                                                                              Viewed 14 times in the last 48 hours
                                                                                Exceptional! 5.0/5
                                                                                (10 reviews)
                                                                                avg/night
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 6
                                                                                House #693973vb
                                                                                10
                                                                                Viewed 6 times in the last 48 hours
                                                                                  Excellent! 4.7/5
                                                                                  (7 reviews)
                                                                                  avg/night
                                                                                  • 4 BR
                                                                                  • 1 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 8
                                                                                  House #700566vb
                                                                                  7
                                                                                  Viewed 13 times in the last 48 hours
                                                                                    Exceptional! 5.0/5
                                                                                    (10 reviews)
                                                                                    avg/night
                                                                                    • 10 BR
                                                                                    • 8 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 22
                                                                                    House #782817vb
                                                                                    10
                                                                                    Viewed 27 times in the last 48 hours
                                                                                      • 3 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 8
                                                                                      House #851219vb
                                                                                      2
                                                                                      Viewed 13 times in the last 48 hours
                                                                                        Exceptional! 5.0/5
                                                                                        (39 reviews)
                                                                                        avg/night
                                                                                        • 4 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 8
                                                                                        House #3721423
                                                                                        39
                                                                                        Viewed 8 times in the last 48 hours
                                                                                          Wonderful! 4.8/5
                                                                                          (9 reviews)
                                                                                          avg/night
                                                                                          • 3 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 7
                                                                                          House #701122vb
                                                                                          9
                                                                                          Viewed 6 times in the last 48 hours
                                                                                            • 4 BR
                                                                                            • 2 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 11
                                                                                            House #702723vb
                                                                                            3
                                                                                              • 5 BR
                                                                                              • 4 BA
                                                                                              • Sleeps 10
                                                                                              House #3959837
                                                                                              12
                                                                                              Viewed 27 times in the last 48 hours
                                                                                                avg/night
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 10
                                                                                                House #743337vb
                                                                                                4
                                                                                                Viewed 9 times in the last 48 hours
                                                                                                  Excellent! 4.7/5
                                                                                                  (18 reviews)
                                                                                                  avg/night
                                                                                                  • 9 BR
                                                                                                  • 4 BA
                                                                                                  • Sleeps 20
                                                                                                  House #428459vb
                                                                                                  18
                                                                                                  Viewed 39 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (11 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • 1 HF BA
                                                                                                    • Sleeps 10
                                                                                                    House #580955vb
                                                                                                    11
                                                                                                    Viewed 10 times in the last 48 hours
                                                                                                      Wonderful! 4.8/5
                                                                                                      (5 reviews)
                                                                                                      avg/night
                                                                                                      • 4 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 7
                                                                                                      House #774024vb
                                                                                                      5
                                                                                                      Viewed 16 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Hillsdale: House Rentals (397)

                                                                                                       

                                                                                                      Recent Hillsdale Reviews

                                                                                                      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

                                                                                                      Beautiful property in charming town with wonderful manager

                                                                                                      5 of 5
                                                                                                      I came to stay at the South Lee Schoolhouse to celebrate New Year's Eve and had a wonderful time there. I visited with a party of 6, though there is easily space for a few more. The house is gorgeous with tall ceilings and open spaces. It had available everything we needed, including a fully stocked (and beautiful) kitchen for cooking full meals at home. There is also wood available for a cozy fire in winter. The house has a scenic view, is easy to locate, and is only a short drive from downtown Stockbridge. The owner, Mary, is great. She is easily available if any questions come up, and is very responsive if you should need anything. She really went above and beyond in making our stay happy and smooth. Finally, the area is scenic and filled with great things to do. Since we visited in winter, we went snow shoeing at Hilltop Orchards, for a sleigh ride at SweetBrook Farm, and really enjoyed the hot chocolate menu at the Blantyre. We also loved the Norman Rockwell museum and the Clark Institute. Plus, walking around downtown Stockbridge finds iconic settings and fun shops. Altogether a great stay!
                                                                                                      • Submitted: Jan 15, 2017
                                                                                                      • Stayed: Dec 2016

                                                                                                      Warm, welcoming home for a long weekend

                                                                                                      5 of 5
                                                                                                      We two Manhattan dwellers were invited to a Thanksgiving feast upstate and decided to make a long weekend of it. We found this lovely home and had a wonderful time. Morag Hann greeted us and showed us everything we needed to know before handing over the keys to the home she has decorated so beautifully. The kitchen is large and well-equipped with a large table where we had breakfast every morning, watching chickadees come to the bird feeder just outside the window. There are two large and very comfortable bedrooms upstairs and a cozy den where we watched Netflix movies after dinner out at one of Hudson's great restaurants. There are three clean and well designed bathrooms in the house. There is parking right on the street, because this house is strategically located a few streets away from busy Warren Street, where the shops and restaurants are located. That also meant it was quiet at night, a real treat for these big-city dwellers. During the day, we enjoyed strolling through Hudson and visiting its many stores and art galleries. We also took an excursion to nearby Chatham for more shopping and to meet friends. Overall, a great stay. We will return here!
                                                                                                      • Submitted: Nov 30, 2016
                                                                                                      • Stayed: Nov 2016