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    Wonderful! 4.9/5
    (37 reviews)
    avg/night
    • 3 BR
    • 1 BA
    • Sleeps 6
    House #469617vb
    37
    Viewed 17 times in the last 48 hours
      Wonderful! 4.9/5
      (27 reviews)
      avg/night
      • 3 BR
      • 2 BA
      • Sleeps 12
      House #420727vb
      27
      Viewed 24 times in the last 48 hours
        avg/night
        • 5 BR
        • 3 BA
        • Sleeps 8
        Cottage #425380vb
        3
        Viewed 30 times in the last 48 hours
          Excellent! 4.4/5
          (16 reviews)
          avg/night
          • 3 BR
          • 1 BA
          • Sleeps 6
          Cottage #203288vb
          16
          Viewed 35 times in the last 48 hours
            Wonderful! 4.8/5
            (24 reviews)
            avg/night
            • 1 BR
            • 1 BA
            • Sleeps 4
            House #310035vb
            24
            Viewed 33 times in the last 48 hours
              Excellent! 4.7/5
              (15 reviews)
              avg/night
              • 1 BR
              • 1 BA
              • Sleeps 4
              Apartment #133082
              15
              Viewed 19 times in the last 48 hours
                avg/night
                • 2 BR
                • 1 BA
                • Sleeps 7
                Cottage #310698
                7
                Viewed 36 times in the last 48 hours
                  avg/night
                  • 3 BR
                  • 3 BA
                  • Sleeps 13
                  Condo #878199vb
                  3
                  Viewed 29 times in the last 48 hours
                    • 3 BR
                    • 2 BA
                    • 1 HF BA
                    • Sleeps 9
                    Condo #595232vb
                    11
                      • 4 BR
                      • 3 BA
                      • 1 HF BA
                      • Sleeps 12
                      House #1020471vb
                      3
                      Viewed 24 times in the last 48 hours
                        Very Good! 4/5
                        (8 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Sleeps 7
                        House #344576vb
                        8
                        Viewed 16 times in the last 48 hours
                          • 5 BR
                          • 3 BA
                          • 2 HF BA
                          • Sleeps 9
                          Estate #802737vb
                          3
                          Viewed 8 times in the last 48 hours
                            avg/night
                            • 4 BR
                            • 2 BA
                            • 1 HF BA
                            • Sleeps 10
                            Townhome #4320036
                            3
                            Viewed 18 times in the last 48 hours
                              avg/night
                              • 8 BR
                              • 5 BA
                              • Sleeps 20
                              House #985738vb
                              Viewed 15 times in the last 48 hours
                                avg/night
                                • 2 BR
                                • 1 BA
                                • Sleeps 5
                                Apartment #1010923vb
                                Viewed 13 times in the last 48 hours
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 4
                                  Apartment #615402vb
                                  4
                                    • 3 BR
                                    • 2 BA
                                    • 1 HF BA
                                    • Sleeps 6
                                    House #1035398vb
                                      • 4 BR
                                      • 3 BA
                                      • 1 HF BA
                                      • Sleeps 8
                                      Townhome #4170111
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 4
                                        Condo #4365894
                                          Exceptional! 5/5
                                          (6 reviews)
                                          avg/night
                                          • 2 BR
                                          • 2 BA
                                          • Sleeps 6
                                          House #804956vb
                                          6
                                          Viewed 73 times in the last 48 hours
                                            Exceptional! 5/5
                                            (22 reviews)
                                            avg/night
                                            • 6 BR
                                            • 5 BA
                                            • Sleeps 20
                                            Estate #4258796
                                            22
                                            Viewed 127 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (9 reviews)
                                              avg/night
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 7
                                              House #330190
                                              9
                                              Viewed 13 times in the last 48 hours
                                                Exceptional! 5/5
                                                (9 reviews)
                                                avg/night
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 6
                                                Cottage #3790476
                                                9
                                                Viewed 12 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (20 reviews)
                                                  avg/night
                                                  • 2 BR
                                                  • 1 BA
                                                  • Sleeps 5
                                                  Cottage #707780vb
                                                  20
                                                  Viewed 35 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 11 times in the last 48 hours
                                                      Wonderful! 4.9/5
                                                      (28 reviews)
                                                      avg/night
                                                      • 5 BR
                                                      • 5 BA
                                                      • Sleeps 12
                                                      House #729783vb
                                                      28
                                                      Viewed 12 times in the last 48 hours
                                                        Wonderful! 4.9/5
                                                        (8 reviews)
                                                        avg/night
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 6
                                                        Condo #3712818
                                                        8
                                                        Viewed 12 times in the last 48 hours
                                                          Excellent! 4.6/5
                                                          (51 reviews)
                                                          avg/night
                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 4
                                                          Cabin #182224
                                                          51
                                                          Viewed 77 times in the last 48 hours
                                                            avg/night
                                                            • 4 BR
                                                            • 2 BA
                                                            • 1 HF BA
                                                            • Sleeps 8
                                                            House #4222851
                                                            Viewed 8 times in the last 48 hours
                                                              Wonderful! 4.8/5
                                                              (38 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              Cottage #293009
                                                              38
                                                              Viewed 52 times in the last 48 hours
                                                                Excellent! 4.7/5
                                                                (10 reviews)
                                                                avg/night
                                                                • 3 BR
                                                                • 1 BA
                                                                • 1 HF BA
                                                                • Sleeps 6
                                                                Chateau / Country House #4149878
                                                                10
                                                                Viewed 34 times in the last 48 hours
                                                                  Wonderful! 4.8/5
                                                                  (22 reviews)
                                                                  avg/night
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 5
                                                                  Cabin #189705vb
                                                                  22
                                                                  Viewed 51 times in the last 48 hours
                                                                    Wonderful! 4.8/5
                                                                    (21 reviews)
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • Sleeps 8
                                                                    House #236935vb
                                                                    21
                                                                    Viewed 10 times in the last 48 hours
                                                                      Exceptional! 5/5
                                                                      (14 reviews)
                                                                      avg/night
                                                                      • 5 BR
                                                                      • 2 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 10
                                                                      Barn #616214vb
                                                                      14
                                                                      Viewed 44 times in the last 48 hours
                                                                        Wonderful! 4.8/5
                                                                        (20 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 3 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 10
                                                                        House #272149vb
                                                                        20
                                                                        Viewed 34 times in the last 48 hours
                                                                          Excellent! 4.7/5
                                                                          (6 reviews)
                                                                          avg/night
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 8
                                                                          Bungalow #717959vb
                                                                          6
                                                                          Viewed 5 times in the last 48 hours
                                                                            Exceptional! 5/5
                                                                            (19 reviews)
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 12
                                                                            House #583082vb
                                                                            19
                                                                            Viewed 33 times in the last 48 hours
                                                                              Wonderful! 4.9/5
                                                                              (10 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              House #892478vb
                                                                              10
                                                                              Viewed 70 times in the last 48 hours
                                                                                Exceptional! 5/5
                                                                                (11 reviews)
                                                                                avg/night
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 8
                                                                                House #4193492
                                                                                11
                                                                                Viewed 32 times in the last 48 hours
                                                                                  Wonderful! 4.8/5
                                                                                  (25 reviews)
                                                                                  avg/night
                                                                                  • 2 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  Condo #238631vb
                                                                                  25
                                                                                  Viewed 32 times in the last 48 hours
                                                                                    Exceptional! 5/5
                                                                                    (10 reviews)
                                                                                    avg/night
                                                                                    • 6 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 10
                                                                                    House #4064007
                                                                                    10
                                                                                    Viewed 24 times in the last 48 hours
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 10
                                                                                      House #570547vb
                                                                                      3
                                                                                      Viewed 20 times in the last 48 hours
                                                                                        Exceptional! 5/5
                                                                                        (6 reviews)
                                                                                        avg/night
                                                                                        • 5 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 8
                                                                                        House #4160350
                                                                                        6
                                                                                        Viewed 14 times in the last 48 hours
                                                                                          Excellent! 4.6/5
                                                                                          (23 reviews)
                                                                                          avg/night
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 10
                                                                                          House #283894vb
                                                                                          23
                                                                                          Viewed 30 times in the last 48 hours
                                                                                            Wonderful! 4.9/5
                                                                                            (34 reviews)
                                                                                            avg/night
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 3
                                                                                            House #135474vb
                                                                                            34
                                                                                            Viewed 20 times in the last 48 hours
                                                                                              Exceptional! 5/5
                                                                                              (16 reviews)
                                                                                              avg/night
                                                                                              • 6 BR
                                                                                              • 5 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 16
                                                                                              House #396147vb
                                                                                              16
                                                                                              Viewed 21 times in the last 48 hours
                                                                                                Wonderful! 4.8/5
                                                                                                (30 reviews)
                                                                                                avg/night
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 8
                                                                                                House #419897vb
                                                                                                30
                                                                                                Viewed 18 times in the last 48 hours
                                                                                                  Good! 3.9/5
                                                                                                  (10 reviews)
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 8
                                                                                                  Cottage #3576605
                                                                                                  10
                                                                                                  Viewed 23 times in the last 48 hours
                                                                                                    Exceptional! 5/5
                                                                                                    (28 reviews)
                                                                                                    avg/night
                                                                                                    • 2 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 6
                                                                                                    Condo #651723vb
                                                                                                    28
                                                                                                    Viewed 15 times in the last 48 hours
                                                                                                      Exceptional! 5/5
                                                                                                      (11 reviews)
                                                                                                      avg/night
                                                                                                      • 7 BR
                                                                                                      • 4 BA
                                                                                                      • Sleeps 24
                                                                                                      Lodge #3967190
                                                                                                      11
                                                                                                      Viewed 27 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Pittsfield Reviews

                                                                                                      BEAUTIFUL, Exceeded my expectations!

                                                                                                      5 of 5
                                                                                                      I rented the Playhouse for a birthday celebration. I have a large family, there were 26 of us, and we have rented houses in the past for different holidays and celebrations. This house is one of the most beautiful and spacious places that we have rented. Everyone had their own space and privacy when needed. The house is so comfortable and has everything you need for a pleasant stay. My nephew is a chef and he prepared an 8 course meal for 26 people. Having the 2 kitchens made this an effortless task. The owner was very accommodating and responsive to my questions. Thank you Daniel for sharing your beautiful home. I would highly recommend this house.
                                                                                                      • Submitted: Mar 18, 2017
                                                                                                      • Stayed: Feb 2017

                                                                                                      We had a lovely and memorable time staying at your home! Will definitely book again!

                                                                                                      5 of 5
                                                                                                      Thank you for sharing your beautiful home with us. The house was clean and full of character! We appreciated the luxurious toiletries and quality bedding and towels. The location is great... as it is 15 min or less driving into the towns of Lenox, Lee, and Pittsfield. It took all of 10 minutes to get to the closest ski area, Bosquet. The backyard was lovely and we enjoyed grilling on the porch and sharing meals with family and friends. The foosball table in the basement was a fun bonus... It was such a joy to hear our kids running and laughing through the halls of your beautiful home!
                                                                                                      • Submitted: Mar 1, 2017
                                                                                                      • Stayed: Feb 2017

                                                                                                      Stylish, comfortable getaway in a scenic setting.

                                                                                                      5 of 5
                                                                                                      We had a wonderful time at Ed and Kathy's Berkshires retreat. Even before we arrived I knew this was the place for us—they were incredibly responsive and helpful in answering our Qs. The house is immaculate; it looks like it walked out of the pages of House Beautiful. The location is perfect; 2.5 hours from Brooklyn and close to little towns like Chatham, plus ski areas, etc. It snowed a lot the weekend we went up, but the property's caretaker came over early and plowed out the driveway, and then he came back to salt the pavement. The kitchen was well stocked; the beds and baths were super comfortable. I'd recommend this property to anyone looking for a chic getaway that blends the quiet seclusion of the country with modern, comfortable amenities!
                                                                                                      • Submitted: Feb 28, 2017
                                                                                                      • Stayed: Feb 2017