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  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
    Exceptional! 5.0/5
    (10 reviews)
    avg/night
    • 5 BR
    • 3 BA
    • Sleeps 14
    House #345355
    10
    Viewed 33 times in the last 48 hours
      Exceptional! 5.0/5
      (10 reviews)
      avg/night
      • 5 BR
      • 3 BA
      • Sleeps 14
      House #259766vb
      10
      Viewed 12 times in the last 48 hours
        Wonderful! 4.9/5
        (23 reviews)
        avg/night
        • 3 BR
        • 2 BA
        • Sleeps 10
        House #340808
        23
        Viewed 59 times in the last 48 hours
          • 3 BR
          • 2 BA
          • Sleeps 20
          Chalet #640519vb
          2
          Viewed 15 times in the last 48 hours
            Exceptional! 5.0/5
            (6 reviews)
            avg/night
            • 4 BR
            • 3 BA
            • Sleeps 10
            House #129127vb
            6
            Viewed 19 times in the last 48 hours
              Excellent! 4.6/5
              (11 reviews)
              avg/night
              • 5 BR
              • 3 BA
              • Sleeps 12
              House #334430
              11
              Viewed 74 times in the last 48 hours
                Wonderful! 4.8/5
                (12 reviews)
                avg/night
                • 5 BR
                • 2 BA
                • Sleeps 12
                House #622687vb
                12
                Viewed 31 times in the last 48 hours
                  Wonderful! 4.8/5
                  (10 reviews)
                  avg/night
                  • 3 BR
                  • 2 BA
                  • Sleeps 8
                  Chalet #3642810
                  10
                  Viewed 15 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 6 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
                        avg/night
                        • 4 BR
                        • 2 BA
                        • Sleeps 11
                        House #759492vb
                        0
                        Viewed 29 times in the last 48 hours
                          Wonderful! 4.8/5
                          (21 reviews)
                          avg/night
                          • 3 BR
                          • 2 BA
                          • Sleeps 10
                          House #166942vb
                          21
                          Viewed 132 times in the last 48 hours
                            • 2 BR
                            • 1 BA
                            • Sleeps 8
                            House #868730vb
                            1
                            Viewed 30 times in the last 48 hours
                              avg/night
                              • 5 BR
                              • 3 BA
                              • Sleeps 16
                              Condo #938633
                              1
                              Viewed 21 times in the last 48 hours
                                avg/night
                                • 4 BR
                                • 2 BA
                                • Sleeps 8
                                House #3861821
                                0
                                Viewed 8 times in the last 48 hours
                                  • 3 BR
                                  • 3 BA
                                  • Sleeps 6
                                  House #764994vb
                                  0
                                  Viewed 32 times in the last 48 hours
                                    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
                                      (89 reviews)
                                      avg/night
                                      • 2 BR
                                      • 1 BA
                                      • 1 HF BA
                                      • Sleeps 5
                                      Cabin #176037
                                      89
                                      Viewed 150 times in the last 48 hours
                                        Wonderful! 4.8/5
                                        (37 reviews)
                                        avg/night
                                        • 5 BR
                                        • 2 BA
                                        • 1 HF BA
                                        • Sleeps 13
                                        House #119086
                                        37
                                        Viewed 93 times in the last 48 hours
                                          Excellent! 4.6/5
                                          (5 reviews)
                                          avg/night
                                          • 4 BR
                                          • 2 BA
                                          • Sleeps 10
                                          Condo #104286
                                          5
                                          Viewed 32 times in the last 48 hours
                                            Wonderful! 4.8/5
                                            (9 reviews)
                                            avg/night
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 4
                                            Cabin #754153vb
                                            9
                                            Viewed 30 times in the last 48 hours
                                              avg/night
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 4
                                              Condo #846796vb
                                              4
                                              Viewed 15 times in the last 48 hours
                                                avg/night
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 6
                                                Condo #628992vb
                                                3
                                                Viewed 34 times in the last 48 hours
                                                  avg/night
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 4
                                                  Apartment #4053247
                                                  2
                                                  Viewed 47 times in the last 48 hours
                                                    Wonderful! 4.9/5
                                                    (33 reviews)
                                                    avg/night
                                                    • 4 BR
                                                    • 2 BA
                                                    • Sleeps 10
                                                    House #3809315
                                                    33
                                                    Viewed 22 times in the last 48 hours
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 4
                                                      Condo #3840565
                                                      0
                                                      Viewed 70 times in the last 48 hours
                                                        Exceptional! 5.0/5
                                                        (29 reviews)
                                                        avg/night
                                                        • 2 BR
                                                        • 3 BA
                                                        • Sleeps 6
                                                        House #411999vb
                                                        29
                                                        Viewed 7 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (14 reviews)
                                                          avg/night
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 4
                                                          Condo #758489vb
                                                          14
                                                          Viewed 7 times in the last 48 hours
                                                            avg/night
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                            Cottage #4272059
                                                            3
                                                            Viewed 13 times in the last 48 hours
                                                              Wonderful! 4.8/5
                                                              (11 reviews)
                                                              avg/night
                                                              • 5 BR
                                                              • 3 BA
                                                              • Sleeps 18
                                                              House #4086336
                                                              11
                                                              Viewed 122 times in the last 48 hours
                                                                Wonderful! 4.8/5
                                                                (9 reviews)
                                                                avg/night
                                                                • 3 BR
                                                                • 1 BA
                                                                • Sleeps 8
                                                                Cottage #3929442
                                                                9
                                                                Viewed 20 times in the last 48 hours
                                                                  Excellent! 4.7/5
                                                                  (85 reviews)
                                                                  avg/night
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 4
                                                                  Condo #374633vb
                                                                  85
                                                                  Viewed 40 times in the last 48 hours
                                                                    Wonderful! 4.9/5
                                                                    (12 reviews)
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    Condo #4053986
                                                                    12
                                                                    Viewed 9 times in the last 48 hours
                                                                      Excellent! 4.6/5
                                                                      (14 reviews)
                                                                      avg/night
                                                                      • 5 BR
                                                                      • 2 BA
                                                                      • Sleeps 18
                                                                      House #112754
                                                                      14
                                                                      Viewed 89 times in the last 48 hours
                                                                        Excellent! 4.5/5
                                                                        (13 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 8
                                                                        House #104116
                                                                        13
                                                                        Viewed 38 times in the last 48 hours
                                                                          avg/night
                                                                          • 5 BR
                                                                          • 2 BA
                                                                          • Sleeps 7
                                                                          House #495543vb
                                                                          4
                                                                          Viewed 9 times in the last 48 hours
                                                                            Exceptional! 5.0/5
                                                                            (19 reviews)
                                                                            avg/night
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 4
                                                                            Cabin #401479vb
                                                                            19
                                                                            Viewed 74 times in the last 48 hours
                                                                              Excellent! 4.4/5
                                                                              (16 reviews)
                                                                              avg/night
                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Sleeps 4
                                                                              Condo #264900
                                                                              16
                                                                              Viewed 78 times in the last 48 hours
                                                                                Exceptional! 5.0/5
                                                                                (23 reviews)
                                                                                avg/night
                                                                                • 7 BR
                                                                                • 4 BA
                                                                                • Sleeps 24
                                                                                Farmhouse #3839959
                                                                                23
                                                                                Viewed 65 times in the last 48 hours
                                                                                  Excellent! 4.6/5
                                                                                  (5 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 6
                                                                                  Cottage #256292
                                                                                  5
                                                                                  Viewed 10 times in the last 48 hours
                                                                                    Wonderful! 4.8/5
                                                                                    (37 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 6
                                                                                    Condo #128197
                                                                                    37
                                                                                    Viewed 68 times in the last 48 hours
                                                                                      Wonderful! 4.9/5
                                                                                      (9 reviews)
                                                                                      avg/night
                                                                                      • 4 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 7
                                                                                      House #258826vb
                                                                                      9
                                                                                      Viewed 16 times in the last 48 hours
                                                                                        Exceptional! 5.0/5
                                                                                        (14 reviews)
                                                                                        avg/night
                                                                                        • 3 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 10
                                                                                        House #3992583
                                                                                        14
                                                                                        Viewed 59 times in the last 48 hours
                                                                                          Wonderful! 4.9/5
                                                                                          (41 reviews)
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          Condo #221835
                                                                                          41
                                                                                          Viewed 79 times in the last 48 hours
                                                                                            Excellent! 4.7/5
                                                                                            (7 reviews)
                                                                                            avg/night
                                                                                            • 5 BR
                                                                                            • 3 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 13
                                                                                            House #853465vb
                                                                                            7
                                                                                            Viewed 78 times in the last 48 hours
                                                                                              Exceptional! 5.0/5
                                                                                              (23 reviews)
                                                                                              avg/night
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 14
                                                                                              Lodge #263450vb
                                                                                              23
                                                                                              Viewed 28 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (8 reviews)
                                                                                                avg/night
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 4
                                                                                                Condo #772841vb
                                                                                                8
                                                                                                Viewed 73 times in the last 48 hours
                                                                                                  avg/night
                                                                                                  • 7 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 15
                                                                                                  House #127098
                                                                                                  4
                                                                                                  Viewed 24 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (37 reviews)
                                                                                                    avg/night
                                                                                                    • 4 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 12
                                                                                                    House #211351
                                                                                                    37
                                                                                                    Viewed 41 times in the last 48 hours
                                                                                                      Wonderful! 4.8/5
                                                                                                      (13 reviews)
                                                                                                      avg/night
                                                                                                      • 4 BR
                                                                                                      • 3 BA
                                                                                                      • Sleeps 12
                                                                                                      Chalet #788299vb
                                                                                                      13
                                                                                                      Viewed 60 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Pittsfield: Vacation Rentals (591)

                                                                                                       

                                                                                                      Recent Pittsfield Reviews

                                                                                                      Great place for an extended stay

                                                                                                      5 of 5
                                                                                                      We stayed at this house over a long holiday weekend for our skiing and snowboarding trip. It was very conveniently located not even 30 minutes away from Killington Mountain, with a rental shop on the way. The house is located in a rather private area with no neighboring houses in sight. It is a bit dated on the interior, but it is very well kept and quite a few things have been updated, like the master bathroom. There were plenty of items left around to make us comfortable, ranging from tons of towels, to DVDs, books, and kitchen supplies. Interior has a nice communal area with the combined living room and dining room creating a nice open atmosphere. The owner is very accommodating and incredibly easy to communicate with. Would stay there again given the opportunity.
                                                                                                      • Submitted: Jan 16, 2017
                                                                                                      • Stayed: Jan 2017

                                                                                                      Nothing short of amazing!!!

                                                                                                      5 of 5
                                                                                                      This house was nothing short of amazing. From the interior decor to the endless property outside, it was so worth every dollar and I will definitely be back! The pictures are accurate and the different living areas were perfect for Girl talk in one room while the guys watched football in the other. The fireplace was my absolute fav!! This property is extremely close to the mountains. We went snowmobiling which was literally 5 mins away. We also snow tubed and skied in the Killington resort which is about 15 mins. Just be advised that the pots are NOT none stick so you may wanna bring a few of your favorite comfortable cooking pots. Other than that everything was great!!
                                                                                                      • Submitted: Jan 14, 2017
                                                                                                      • Stayed: Jan 2017

                                                                                                      Cozy, Well-Equipped, Wonderful Winter Escape with Excellent Host

                                                                                                      5 of 5
                                                                                                      My friends and I rented Dave's residence for a New Years getaway and we couldn't have asked for a better place to stay nor a more accommodating host. Dave was extremely professional and helpful in the weeks leading up to the stay. The house itself is exactly as described in the description and there were no issues to be found anywhere. Everything was clean, well-stocked, and maintained excellently. I would definitely recommend this place to friends and contact Dave again for any future bookings for similar trips.
                                                                                                      • Submitted: Jan 13, 2017
                                                                                                      • Stayed: Dec 2016