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  • Showing 1-50 of 300+
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    Wonderful! 4.9/5
    (36 reviews)
    avg/night
    • 3 BR
    • 1 BA
    • Sleeps 6
    House #469617vb
    36
    Viewed 19 times in the last 48 hours
      Wonderful! 4.9/5
      (27 reviews)
      avg/night
      • 3 BR
      • 2 BA
      • Sleeps 12
      House #420727vb
      27
      Viewed 22 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 49 times in the last 48 hours
          Wonderful! 4.8/5
          (23 reviews)
          avg/night
          • 1 BR
          • 1 BA
          • Sleeps 4
          House #310035vb
          23
          Viewed 17 times in the last 48 hours
            Excellent! 4.4/5
            (15 reviews)
            avg/night
            • 3 BR
            • 1 BA
            • Sleeps 6
            Cottage #203288vb
            15
            Viewed 32 times in the last 48 hours
              Excellent! 4.6/5
              (14 reviews)
              avg/night
              • 1 BR
              • 1 BA
              • Sleeps 4
              Apartment #133082
              14
              Viewed 23 times in the last 48 hours
                Wonderful! 4.9/5
                (9 reviews)
                avg/night
                • 3 BR
                • 2 BA
                • 1 HF BA
                • Sleeps 9
                Condo #595232vb
                9
                Viewed 47 times in the last 48 hours
                  avg/night
                  • 2 BR
                  • 1 BA
                  • Sleeps 7
                  Cottage #310698
                  6
                  Viewed 18 times in the last 48 hours
                    avg/night
                    • 5 BR
                    • 3 BA
                    • Sleeps 8
                    Cottage #425380vb
                    3
                    Viewed 35 times in the last 48 hours
                      • 5 BR
                      • 3 BA
                      • 2 HF BA
                      • Sleeps 9
                      Estate #802737vb
                      1
                      Viewed 9 times in the last 48 hours
                        avg/night
                        • 2 BR
                        • 1 BA
                        • Sleeps 6
                        House #4113926
                        1
                        Viewed 11 times in the last 48 hours
                          avg/night
                          • 3 BR
                          • 3 BA
                          • Sleeps 13
                          Condo #878199vb
                          1
                          Viewed 30 times in the last 48 hours
                            avg/night
                            • 4 BR
                            • 2 BA
                            • 1 HF BA
                            • Sleeps 10
                            Townhome #4320036
                            1
                            Viewed 51 times in the last 48 hours
                              • 2 BR
                              • 1 BA
                              • Sleeps 4
                              Apartment #615402vb
                              4
                                • 4 BR
                                • 3 BA
                                • 1 HF BA
                                • Sleeps 8
                                Townhome #4170111
                                0
                                  avg/night
                                  • 8 BR
                                  • 5 BA
                                  • Sleeps 20
                                  House #985738vb
                                  0
                                  Viewed 10 times in the last 48 hours
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 4
                                    Condo #4365894
                                    0
                                      Exceptional! 5.0/5
                                      (6 reviews)
                                      avg/night
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 6
                                      House #804956vb
                                      6
                                      Viewed 5 times in the last 48 hours
                                        Exceptional! 5.0/5
                                        (14 reviews)
                                        avg/night
                                        • 6 BR
                                        • 5 BA
                                        • Sleeps 20
                                        Estate #4258796
                                        14
                                        Viewed 157 times in the last 48 hours
                                          Wonderful! 4.9/5
                                          (9 reviews)
                                          avg/night
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 7
                                          House #330190
                                          9
                                          Viewed 8 times in the last 48 hours
                                            Wonderful! 4.9/5
                                            (20 reviews)
                                            avg/night
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 5
                                            Cottage #707780vb
                                            20
                                            Viewed 25 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (10 reviews)
                                              avg/night
                                              • 4 BR
                                              • 2 BA
                                              • 1 HF BA
                                              • Sleeps 8
                                              Farmhouse #627684vb
                                              10
                                              Viewed 9 times in the last 48 hours
                                                Excellent! 4.6/5
                                                (49 reviews)
                                                avg/night
                                                • 2 BR
                                                • 1 BA
                                                • Sleeps 4
                                                Cabin #182224
                                                49
                                                Viewed 40 times in the last 48 hours
                                                  Wonderful! 4.8/5
                                                  (38 reviews)
                                                  avg/night
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  Cottage #293009
                                                  38
                                                  Viewed 62 times in the last 48 hours
                                                    Wonderful! 4.8/5
                                                    (22 reviews)
                                                    avg/night
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 5
                                                    Cabin #189705vb
                                                    22
                                                    Viewed 31 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 34 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 15 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 19 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 43 times in the last 48 hours
                                                              Exceptional! 5.0/5
                                                              (10 reviews)
                                                              avg/night
                                                              • 6 BR
                                                              • 3 BA
                                                              • Sleeps 10
                                                              House #4064007
                                                              10
                                                              Viewed 34 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 23 times in the last 48 hours
                                                                  Exceptional! 5.0/5
                                                                  (10 reviews)
                                                                  avg/night
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 8
                                                                  House #4193492
                                                                  10
                                                                  Viewed 23 times in the last 48 hours
                                                                    Wonderful! 4.8/5
                                                                    (9 reviews)
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • Sleeps 5
                                                                    Farmhouse #719766vb
                                                                    9
                                                                    Viewed 18 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (32 reviews)
                                                                      avg/night
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 3
                                                                      House #135474vb
                                                                      32
                                                                      Viewed 28 times in the last 48 hours
                                                                        Excellent! 4.4/5
                                                                        (11 reviews)
                                                                        avg/night
                                                                        • 2 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                        House #3860654
                                                                        11
                                                                        Viewed 37 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (10 reviews)
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 6
                                                                          Cottage #361931vb
                                                                          10
                                                                          Viewed 40 times in the last 48 hours
                                                                            Exceptional! 5.0/5
                                                                            (5 reviews)
                                                                            avg/night
                                                                            • 5 BR
                                                                            • 3 BA
                                                                            • Sleeps 8
                                                                            House #4160350
                                                                            5
                                                                            Viewed 11 times in the last 48 hours
                                                                              Wonderful! 4.9/5
                                                                              (14 reviews)
                                                                              avg/night
                                                                              • 5 BR
                                                                              • 3 BA
                                                                              • Sleeps 10
                                                                              House #603552vb
                                                                              14
                                                                              Viewed 26 times in the last 48 hours
                                                                                Good! 3.9/5
                                                                                (10 reviews)
                                                                                avg/night
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 8
                                                                                Cottage #3576605
                                                                                10
                                                                                Viewed 20 times in the last 48 hours
                                                                                  Wonderful! 4.9/5
                                                                                  (15 reviews)
                                                                                  avg/night
                                                                                  • 2 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  House #3720156
                                                                                  15
                                                                                  Viewed 17 times in the last 48 hours
                                                                                    Wonderful! 4.9/5
                                                                                    (10 reviews)
                                                                                    avg/night
                                                                                    • 4 BR
                                                                                    • 4 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 12
                                                                                    House #4050256
                                                                                    10
                                                                                    Viewed 66 times in the last 48 hours
                                                                                      Wonderful! 4.8/5
                                                                                      (11 reviews)
                                                                                      avg/night
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 4
                                                                                      Apartment #437137vb
                                                                                      11
                                                                                      Viewed 37 times in the last 48 hours
                                                                                        Wonderful! 4.9/5
                                                                                        (10 reviews)
                                                                                        avg/night
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        Cottage #554803vb
                                                                                        10
                                                                                          Wonderful! 4.8/5
                                                                                          (5 reviews)
                                                                                          avg/night
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 8
                                                                                          Bungalow #717959vb
                                                                                          5
                                                                                          Viewed 5 times in the last 48 hours
                                                                                            Excellent! 4.7/5
                                                                                            (27 reviews)
                                                                                            avg/night
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 8
                                                                                            House #419897vb
                                                                                            27
                                                                                            Viewed 38 times in the last 48 hours
                                                                                              Wonderful! 4.8/5
                                                                                              (6 reviews)
                                                                                              avg/night
                                                                                              • 4 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 10
                                                                                              Chalet #793621vb
                                                                                              6
                                                                                              Viewed 29 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 18 times in the last 48 hours
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 10
                                                                                                  House #471272vb
                                                                                                  0
                                                                                                  Viewed 11 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 9 times in the last 48 hours
                                                                                                      Wonderful! 4.9/5
                                                                                                      (9 reviews)
                                                                                                      avg/night
                                                                                                      • 2 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
                                                                                                      House #892478vb
                                                                                                      9
                                                                                                      Viewed 49 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Pittsfield: Vacation Rentals (345)

                                                                                                       

                                                                                                      Recent Pittsfield 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

                                                                                                      Amazing house for large group

                                                                                                      5 of 5
                                                                                                      Stayed here for a four day weekend to celebrate New Years with a group of ten of us. The house was perfect could not ask for a more accommodating place to get away from the city and relax with friends. There was more than enough room where ten adults felt spread out and there where extra beds and a futon still empty. The layout of the house is ideal all the bedrooms are upstairs with an extra tv space. The down stairs is a large open space with living room, dining room, and the kitchen. We had a chef come and cook for us for NYE and it was great being able to spread out in one room. Went skiing a few days at Jiminy Peak which is less than an hour drive. Every one already can't wait to return in the summer.
                                                                                                      • Submitted: Jan 5, 2017
                                                                                                      • Stayed: Dec 2016

                                                                                                      Beautiful Retreat

                                                                                                      5 of 5
                                                                                                      Cabin is beautiful, well appointed with everything you might need to hide in the woods for awhile. We stayed for a week to get away from the city and sunk into the calm, quiet warmth. Cannot recommend enough!
                                                                                                      • Submitted: Dec 31, 2016
                                                                                                      • Stayed: Dec 2016