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    Exceptional! 5.0/5
    (10 reviews)
    avg/night
    • 5 BR
    • 3 BA
    • Sleeps 14
    House #345355
    10
    Viewed 20 times in the last 48 hours
      Exceptional! 5.0/5
      (10 reviews)
      avg/night
      • 5 BR
      • 3 BA
      • Sleeps 14
      House #259766vb
      10
      Viewed 5 times in the last 48 hours
        Wonderful! 4.8/5
        (24 reviews)
        avg/night
        • 3 BR
        • 2 BA
        • Sleeps 10
        House #340808
        24
        Viewed 9 times in the last 48 hours
          • 3 BR
          • 2 BA
          • Sleeps 20
          Chalet #640519vb
          2
          Viewed 12 times in the last 48 hours
            Exceptional! 5.0/5
            (6 reviews)
            avg/night
            • 4 BR
            • 3 BA
            • Sleeps 10
            House #129127vb
            6
            Viewed 9 times in the last 48 hours
              Excellent! 4.7/5
              (12 reviews)
              avg/night
              • 5 BR
              • 3 BA
              • Sleeps 12
              House #334430
              12
              Viewed 10 times in the last 48 hours
                avg/night
                • 3 BR
                • 2 BA
                • Sleeps 8
                Chalet #4335951
                2
                Viewed 6 times in the last 48 hours
                  Wonderful! 4.8/5
                  (12 reviews)
                  avg/night
                  • 5 BR
                  • 2 BA
                  • Sleeps 12
                  House #622687vb
                  12
                  Viewed 16 times in the last 48 hours
                    Excellent! 4.7/5
                    (11 reviews)
                    avg/night
                    • 3 BR
                    • 2 BA
                    • Sleeps 8
                    Chalet #3642810
                    11
                    Viewed 6 times in the last 48 hours
                      Wonderful! 4.9/5
                      (57 reviews)
                      avg/night
                      • 3 BR
                      • 2 BA
                      • 1 HF BA
                      • Sleeps 15
                      House #148104vb
                      57
                      Viewed 12 times in the last 48 hours
                        Wonderful! 4.8/5
                        (21 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Sleeps 10
                        House #166942vb
                        21
                        Viewed 14 times in the last 48 hours
                          Wonderful! 4.9/5
                          (9 reviews)
                          avg/night
                          • 3 BR
                          • 1 BA
                          • 1 HF BA
                          • Sleeps 8
                          House #429854vb
                          9
                            • 2 BR
                            • 1 BA
                            • Sleeps 8
                            Condo #868730vb
                            4
                              • 4 BR
                              • 2 BA
                              • Sleeps 11
                              House #759492vb
                              1
                                • 5 BR
                                • 3 BA
                                • Sleeps 16
                                Condo #938633
                                2
                                  • 3 BR
                                  • 3 BA
                                  • Sleeps 6
                                  House #764994vb
                                    • 4 BR
                                    • 2 BA
                                    • Sleeps 8
                                    House #3861821
                                      Excellent! 4.7/5
                                      (9 reviews)
                                      View details for price
                                      • 3 BR
                                      • 2 BA
                                      • 1 HF BA
                                      • Sleeps 6
                                      House #4328487
                                      9
                                        Exceptional! 5.0/5
                                        (97 reviews)
                                        avg/night
                                        • 2 BR
                                        • 1 BA
                                        • 1 HF BA
                                        • Sleeps 5
                                        Cabin #176037
                                        97
                                        Viewed 126 times in the last 48 hours
                                          Wonderful! 4.8/5
                                          (39 reviews)
                                          avg/night
                                          • 5 BR
                                          • 2 BA
                                          • 1 HF BA
                                          • Sleeps 13
                                          House #119086
                                          39
                                          Viewed 75 times in the last 48 hours
                                            Excellent! 4.6/5
                                            (5 reviews)
                                            avg/night
                                            • 4 BR
                                            • 2 BA
                                            • Sleeps 10
                                            Condo #104286
                                            5
                                            Viewed 38 times in the last 48 hours
                                              avg/night
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 4
                                              Condo #846796vb
                                              4
                                              Viewed 63 times in the last 48 hours
                                                Wonderful! 4.8/5
                                                (9 reviews)
                                                avg/night
                                                • 2 BR
                                                • 1 BA
                                                • Sleeps 4
                                                Cabin #754153vb
                                                9
                                                Viewed 53 times in the last 48 hours
                                                  avg/night
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 4
                                                  Apartment #4053247
                                                  2
                                                  Viewed 22 times in the last 48 hours
                                                    Wonderful! 4.9/5
                                                    (36 reviews)
                                                    avg/night
                                                    • 4 BR
                                                    • 2 BA
                                                    • Sleeps 10
                                                    House #3809315
                                                    36
                                                    Viewed 15 times in the last 48 hours
                                                      avg/night
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      Condo #628992vb
                                                      3
                                                      Viewed 27 times in the last 48 hours
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        Condo #3840565
                                                        Viewed 20 times in the last 48 hours
                                                          Excellent! 4.5/5
                                                          (15 reviews)
                                                          avg/night
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 8
                                                          House #104116
                                                          15
                                                          Viewed 27 times in the last 48 hours
                                                            avg/night
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                            Cottage #4272059
                                                            3
                                                            Viewed 12 times in the last 48 hours
                                                              Excellent! 4.7/5
                                                              (85 reviews)
                                                              avg/night
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 4
                                                              Condo #374633vb
                                                              85
                                                              Viewed 15 times in the last 48 hours
                                                                Exceptional! 5.0/5
                                                                (19 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                Cabin #401479vb
                                                                19
                                                                Viewed 21 times in the last 48 hours
                                                                  Exceptional! 5.0/5
                                                                  (23 reviews)
                                                                  avg/night
                                                                  • 7 BR
                                                                  • 4 BA
                                                                  • Sleeps 24
                                                                  Farmhouse #3839959
                                                                  23
                                                                  Viewed 57 times in the last 48 hours
                                                                    Wonderful! 4.8/5
                                                                    (9 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 1 BA
                                                                    • Sleeps 8
                                                                    Cottage #3929442
                                                                    9
                                                                    Viewed 24 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (16 reviews)
                                                                      avg/night
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      Condo #758489vb
                                                                      16
                                                                      Viewed 9 times in the last 48 hours
                                                                        Wonderful! 4.8/5
                                                                        (12 reviews)
                                                                        avg/night
                                                                        • 5 BR
                                                                        • 3 BA
                                                                        • Sleeps 18
                                                                        House #4086336
                                                                        12
                                                                        Viewed 86 times in the last 48 hours
                                                                          Excellent! 4.6/5
                                                                          (15 reviews)
                                                                          avg/night
                                                                          • 5 BR
                                                                          • 2 BA
                                                                          • Sleeps 18
                                                                          House #112754
                                                                          15
                                                                          Viewed 31 times in the last 48 hours
                                                                            avg/night
                                                                            • 5 BR
                                                                            • 2 BA
                                                                            • Sleeps 7
                                                                            House #495543vb
                                                                            4
                                                                            Viewed 6 times in the last 48 hours
                                                                              Exceptional! 5.0/5
                                                                              (32 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 3 BA
                                                                              • Sleeps 6
                                                                              House #411999vb
                                                                              32
                                                                              Viewed 5 times in the last 48 hours
                                                                                Exceptional! 5.0/5
                                                                                (52 reviews)
                                                                                $95
                                                                                avg/night
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 4
                                                                                Apartment #354330
                                                                                52
                                                                                Viewed 55 times in the last 48 hours
                                                                                  Wonderful! 4.8/5
                                                                                  (9 reviews)
                                                                                  avg/night
                                                                                  • 5 BR
                                                                                  • 3 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 13
                                                                                  House #853465vb
                                                                                  9
                                                                                  Viewed 48 times in the last 48 hours
                                                                                    Wonderful! 4.8/5
                                                                                    (9 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 6
                                                                                    Condo #4225962
                                                                                    9
                                                                                    Viewed 33 times in the last 48 hours
                                                                                      Wonderful! 4.8/5
                                                                                      (39 reviews)
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                      Condo #128197
                                                                                      39
                                                                                      Viewed 44 times in the last 48 hours
                                                                                        Wonderful! 4.9/5
                                                                                        (13 reviews)
                                                                                        avg/night
                                                                                        • 3 BR
                                                                                        • 1 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 8
                                                                                        Lodge #432099vb
                                                                                        13
                                                                                        Viewed 12 times in the last 48 hours
                                                                                          Exceptional! 5.0/5
                                                                                          (15 reviews)
                                                                                          avg/night
                                                                                          • 3 BR
                                                                                          • 3 BA
                                                                                          • Sleeps 10
                                                                                          House #3992583
                                                                                          15
                                                                                          Viewed 53 times in the last 48 hours
                                                                                            Excellent! 4.7/5
                                                                                            (10 reviews)
                                                                                            avg/night
                                                                                            • 5 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 10
                                                                                            Chalet #478821vb
                                                                                            10
                                                                                            Viewed 19 times in the last 48 hours
                                                                                              Excellent! 4.5/5
                                                                                              (19 reviews)
                                                                                              avg/night
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              Condo #264900
                                                                                              19
                                                                                              Viewed 24 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (9 reviews)
                                                                                                avg/night
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 4
                                                                                                Condo #967638vb
                                                                                                9
                                                                                                Viewed 16 times in the last 48 hours
                                                                                                  Wonderful! 4.9/5
                                                                                                  (39 reviews)
                                                                                                  avg/night
                                                                                                  • 4 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 12
                                                                                                  House #211351
                                                                                                  39
                                                                                                  Viewed 30 times in the last 48 hours
                                                                                                    Exceptional! 5.0/5
                                                                                                    (24 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 14
                                                                                                    Lodge #263450vb
                                                                                                    24
                                                                                                    Viewed 20 times in the last 48 hours
                                                                                                      Excellent! 4.4/5
                                                                                                      (5 reviews)
                                                                                                      avg/night
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 4
                                                                                                      Condo #268757vb
                                                                                                      5
                                                                                                      Viewed 8 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Pittsfield: Houses, Condos & More (300+)

                                                                                                       

                                                                                                      Recent Pittsfield Reviews

                                                                                                      Perfect Ski Weekend!

                                                                                                      5 of 5
                                                                                                      We had a great time in Woodstock at this rental! The property was close enough to the small, adorable town of Woodstock, but the house itself was off the beaten path and very private. It's a short 25 minute drive from Killington where we went skiing Friday and Saturday. The property has a lot of the original features of the house, but is updated well. The house was very clean and the beds were comfortable. The kitchen has everything you would need to cook in some nights. I would definitely return to this property!
                                                                                                      • Submitted: Feb 19, 2017
                                                                                                      • Stayed: Feb 2017

                                                                                                      Quiet and charming

                                                                                                      5 of 5
                                                                                                      My girlfriend and I had a very relaxing stay with our dogs. The movie projector and hot tub was great!
                                                                                                      • Submitted: Feb 15, 2017
                                                                                                      • Stayed: Feb 2017

                                                                                                      Perfect House for Large Groups

                                                                                                      5 of 5
                                                                                                      Honestly, I was hesitant to rent this house based on the other review but it could not have been more wrong. We did get spotty service while using our navigation on the way to the house, however, the directions the rental office gave were very detailed and we made it there with no problems (it's just a few minutes off the main road and honestly, you're in the mountains so it's to be expected). The house is fairly secluded but we all considered this to be a plus and couldn't wait to enjoy the beautiful view the house offered from the outdoor hot tub. We chose the house so we could spend Saturday skiing at Killington since it is only a 10 minute drive from the house. The layout of the house was also great for our large group since the living area, dining room and kitchen are all open and we were all able to sleep very comfortably. I even hope to book the house again next year. If you're looking for a house for a large group you can't get much better than this.
                                                                                                      • Submitted: Feb 13, 2017
                                                                                                      • Stayed: Feb 2017