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  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
    Exceptional! 5.0/5
    (15 reviews)
    avg/night
    • 6 BR
    • 5 BA
    • Sleeps 20
    Estate #4258796
    15
    Viewed 165 times in the last 48 hours
      Wonderful! 4.9/5
      (9 reviews)
      avg/night
      • 3 BR
      • 2 BA
      • Sleeps 7
      House #330190
      9
        Wonderful! 4.9/5
        (10 reviews)
        avg/night
        • 4 BR
        • 2 BA
        • 1 HF BA
        • Sleeps 8
        Farmhouse #627684vb
        10
        Viewed 10 times in the last 48 hours
          Wonderful! 4.9/5
          (23 reviews)
          avg/night
          • 5 BR
          • 5 BA
          • Sleeps 12
          House #729783vb
          23
          Viewed 22 times in the last 48 hours
            Wonderful! 4.8/5
            (24 reviews)
            avg/night
            • 7 BR
            • 3 BA
            • Sleeps 10
            Farmhouse #444851vb
            24
            Viewed 59 times in the last 48 hours
              Excellent! 4.7/5
              (10 reviews)
              avg/night
              • 3 BR
              • 1 BA
              • 1 HF BA
              • Sleeps 6
              Chateau / Country House #4149878
              10
              Viewed 59 times in the last 48 hours
                Exceptional! 5.0/5
                (16 reviews)
                avg/night
                • 3 BR
                • 1 BA
                • 1 HF BA
                • Sleeps 8
                House #3811779
                16
                Viewed 28 times in the last 48 hours
                  Very Good! 4.0/5
                  (8 reviews)
                  avg/night
                  • 3 BR
                  • 2 BA
                  • Sleeps 7
                  House #344576vb
                  8
                  Viewed 46 times in the last 48 hours
                    Wonderful! 4.9/5
                    (27 reviews)
                    avg/night
                    • 3 BR
                    • 2 BA
                    • Sleeps 12
                    House #420727vb
                    27
                    Viewed 18 times in the last 48 hours
                      Exceptional! 5.0/5
                      (8 reviews)
                      avg/night
                      • 7 BR
                      • 4 BA
                      • Sleeps 24
                      Lodge #3967190
                      8
                      Viewed 109 times in the last 48 hours
                        Wonderful! 4.8/5
                        (9 reviews)
                        avg/night
                        • 2 BR
                        • 2 BA
                        • Sleeps 5
                        Farmhouse #719766vb
                        9
                        Viewed 11 times in the last 48 hours
                          Exceptional! 5.0/5
                          (10 reviews)
                          avg/night
                          • 3 BR
                          • 2 BA
                          • Sleeps 8
                          House #4193492
                          10
                          Viewed 11 times in the last 48 hours
                            Wonderful! 4.9/5
                            (32 reviews)
                            avg/night
                            • 1 BR
                            • 1 BA
                            • Sleeps 3
                            House #135474vb
                            32
                            Viewed 22 times in the last 48 hours
                              Exceptional! 5.0/5
                              (5 reviews)
                              avg/night
                              • 5 BR
                              • 3 BA
                              • Sleeps 8
                              House #4160350
                              5
                              Viewed 13 times in the last 48 hours
                                Excellent! 4.4/5
                                (12 reviews)
                                avg/night
                                • 2 BR
                                • 1 BA
                                • Sleeps 4
                                House #3860654
                                12
                                Viewed 34 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 37 times in the last 48 hours
                                    Exceptional! 5.0/5
                                    (20 reviews)
                                    avg/night
                                    • 3 BR
                                    • 3 BA
                                    • Sleeps 8
                                    House #224680
                                    20
                                    Viewed 48 times in the last 48 hours
                                      Wonderful! 4.9/5
                                      (7 reviews)
                                      avg/night
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 6
                                      Condo #3712818
                                      7
                                      Viewed 18 times in the last 48 hours
                                        Wonderful! 4.9/5
                                        (14 reviews)
                                        avg/night
                                        • 5 BR
                                        • 3 BA
                                        • Sleeps 10
                                        House #603552vb
                                        14
                                        Viewed 21 times in the last 48 hours
                                          Wonderful! 4.9/5
                                          (15 reviews)
                                          avg/night
                                          • 2 BR
                                          • 2 BA
                                          • Sleeps 6
                                          House #3720156
                                          15
                                          Viewed 12 times in the last 48 hours
                                            Excellent! 4.7/5
                                            (22 reviews)
                                            avg/night
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 6
                                            Condo #3471790
                                            22
                                            Viewed 30 times in the last 48 hours
                                              Wonderful! 4.8/5
                                              (11 reviews)
                                              avg/night
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 4
                                              Apartment #437137vb
                                              11
                                              Viewed 24 times in the last 48 hours
                                                Wonderful! 4.9/5
                                                (11 reviews)
                                                avg/night
                                                • 4 BR
                                                • 4 BA
                                                • 1 HF BA
                                                • Sleeps 12
                                                House #4050256
                                                11
                                                Viewed 26 times in the last 48 hours
                                                  Wonderful! 4.8/5
                                                  (24 reviews)
                                                  avg/night
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  Condo #238631vb
                                                  24
                                                  Viewed 17 times in the last 48 hours
                                                    Wonderful! 4.8/5
                                                    (28 reviews)
                                                    avg/night
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 8
                                                    House #419897vb
                                                    28
                                                    Viewed 37 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
                                                        Excellent! 4.4/5
                                                        (15 reviews)
                                                        avg/night
                                                        • 3 BR
                                                        • 1 BA
                                                        • Sleeps 6
                                                        Cottage #203288vb
                                                        15
                                                        Viewed 22 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (36 reviews)
                                                          avg/night
                                                          • 3 BR
                                                          • 1 BA
                                                          • Sleeps 6
                                                          House #469617vb
                                                          36
                                                          Viewed 13 times in the last 48 hours
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 10
                                                            House #471272vb
                                                            Viewed 6 times in the last 48 hours
                                                              Wonderful! 4.9/5
                                                              (10 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              Cottage #554803vb
                                                              10
                                                              Viewed 10 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 32 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 20 times in the last 48 hours
                                                                      avg/night
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      Cottage #872747vb
                                                                      3
                                                                      Viewed 10 times in the last 48 hours
                                                                        Wonderful! 4.9/5
                                                                        (17 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 6
                                                                        House #3893831
                                                                        17
                                                                        Viewed 26 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 8 times in the last 48 hours
                                                                            • 4 BR
                                                                            • 2 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 11
                                                                            House #702723vb
                                                                            3
                                                                              Wonderful! 4.8/5
                                                                              (23 reviews)
                                                                              avg/night
                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Sleeps 4
                                                                              House #310035vb
                                                                              23
                                                                              Viewed 19 times in the last 48 hours
                                                                                • 3 BR
                                                                                • 1 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 6
                                                                                House #4221107
                                                                                13
                                                                                Viewed 34 times in the last 48 hours
                                                                                  Wonderful! 4.8/5
                                                                                  (19 reviews)
                                                                                  avg/night
                                                                                  • 2 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 8
                                                                                  House #236935vb
                                                                                  19
                                                                                    Exceptional! 5.0/5
                                                                                    (26 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 6
                                                                                    Condo #651723vb
                                                                                    26
                                                                                    Viewed 36 times in the last 48 hours
                                                                                      Exceptional! 5.0/5
                                                                                      (14 reviews)
                                                                                      avg/night
                                                                                      • 4 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 10
                                                                                      House #230883vb
                                                                                      14
                                                                                      Viewed 17 times in the last 48 hours
                                                                                        Very Good! 4.1/5
                                                                                        (10 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 6
                                                                                        House #91299vb
                                                                                        10
                                                                                        Viewed 33 times in the last 48 hours
                                                                                          Excellent! 4.7/5
                                                                                          (22 reviews)
                                                                                          avg/night
                                                                                          • 4 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 10
                                                                                          Barn #346642vb
                                                                                          22
                                                                                          Viewed 16 times in the last 48 hours
                                                                                            Wonderful! 4.9/5
                                                                                            (8 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 4
                                                                                            House #3836464
                                                                                            8
                                                                                            Viewed 19 times in the last 48 hours
                                                                                              Wonderful! 4.9/5
                                                                                              (11 reviews)
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 8
                                                                                              Barn #3770158
                                                                                              11
                                                                                              Viewed 44 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (22 reviews)
                                                                                                avg/night
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 6
                                                                                                House #381805vb
                                                                                                22
                                                                                                Viewed 16 times in the last 48 hours
                                                                                                  Exceptional! 5.0/5
                                                                                                  (10 reviews)
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  Condo #786429vb
                                                                                                  10
                                                                                                  Viewed 21 times in the last 48 hours
                                                                                                    Excellent! 4.6/5
                                                                                                    (17 reviews)
                                                                                                    avg/night
                                                                                                    • 5 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 14
                                                                                                    House #3750835
                                                                                                    17
                                                                                                    Viewed 50 times in the last 48 hours
                                                                                                      Exceptional! 5.0/5
                                                                                                      (7 reviews)
                                                                                                      avg/night
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 8
                                                                                                      House #3595415
                                                                                                      7
                                                                                                      Viewed 5 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Jiminy Peak Mountain Resort: Houses, Condos & More (300+)

                                                                                                       

                                                                                                      Recent Jiminy Peak Mountain Resort Reviews

                                                                                                      Relaxing Family Weekend

                                                                                                      5 of 5
                                                                                                      An easy breezy experience from start to end. Howard the owner of the home was kind and gracious in accommodating our large family needs. The home is beautiful and peaceful. Comes with everything you could possibly need. The homes single level and open layout is ideal for little ones. Easy to keep you're eye on them and no stairs to worry about. This a relaxing, comfortable and luxe home located near all the restaurants and shop of Lenox, MA. We had a wonderful time and truly grateful that Howard and Sandy were easy and kind hosts! Thank you!
                                                                                                      • Submitted: Jan 23, 2017
                                                                                                      • Stayed: Jan 2017

                                                                                                      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