Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled
Cancel Clear Filters Apply Filters
More Filters

Price Per Night

$ $

Bedrooms

Bathrooms

Booking Options

Booking Options

Location Type

Features

Managed By

Clear Filters
Use filters to narrow your search results!
Favorite
    Viewed 27 times in the last 48 hours
    6
    Exceptional! 5/5
    (6 reviews)
    avg/night
    Favorite
      Viewed 28 times in the last 48 hours
      16
      Exceptional! 5/5
      (16 reviews)
      avg/night
      Favorite
        3
        avg/night
        Favorite
          Viewed 7 times in the last 48 hours
          6
          Wonderful! 4.8/5
          (6 reviews)
          avg/night
          Favorite
            avg/night
            Favorite
              Viewed 8 times in the last 48 hours
              3
              avg/night
              Favorite
                6
                Excellent! 4.5/5
                (6 reviews)
                avg/night
                Favorite
                  1
                  avg/night
                  Favorite
                    Viewed 10 times in the last 48 hours
                    15
                    Wonderful! 4.9/5
                    (15 reviews)
                    avg/night
                    Favorite
                      Viewed 23 times in the last 48 hours
                      avg/night
                      Favorite
                        avg/night
                        Favorite
                          avg/night
                          Favorite
                            Viewed 114 times in the last 48 hours
                            40
                            Wonderful! 4.9/5
                            (40 reviews)
                            avg/night
                            Favorite
                              Viewed 50 times in the last 48 hours
                              55
                              Wonderful! 4.9/5
                              (55 reviews)
                              avg/night
                              Favorite
                                Viewed 13 times in the last 48 hours
                                5
                                Very Good! 4.2/5
                                (5 reviews)
                                avg/night
                                Favorite
                                  Viewed 14 times in the last 48 hours
                                  14
                                  Wonderful! 4.9/5
                                  (14 reviews)
                                  avg/night
                                  Favorite
                                    Viewed 26 times in the last 48 hours
                                    21
                                    Wonderful! 4.9/5
                                    (21 reviews)
                                    avg/night
                                    Favorite
                                      Viewed 27 times in the last 48 hours
                                      28
                                      Wonderful! 4.9/5
                                      (28 reviews)
                                      avg/night
                                      Favorite
                                        Viewed 12 times in the last 48 hours
                                        18
                                        Wonderful! 4.9/5
                                        (18 reviews)
                                        avg/night
                                        Favorite
                                          Viewed 9 times in the last 48 hours
                                          7
                                          Wonderful! 4.9/5
                                          (7 reviews)
                                          avg/night
                                          Favorite
                                            Viewed 18 times in the last 48 hours
                                            38
                                            Wonderful! 4.8/5
                                            (38 reviews)
                                            avg/night
                                            Favorite
                                              Viewed 52 times in the last 48 hours
                                              34
                                              Wonderful! 4.9/5
                                              (34 reviews)
                                              avg/night
                                              Favorite
                                                Viewed 32 times in the last 48 hours
                                                40
                                                Wonderful! 4.9/5
                                                (40 reviews)
                                                avg/night
                                                Favorite
                                                  Viewed 5 times in the last 48 hours
                                                  9
                                                  Wonderful! 4.8/5
                                                  (9 reviews)
                                                  avg/night
                                                  Favorite
                                                    Viewed 6 times in the last 48 hours
                                                    23
                                                    Wonderful! 4.9/5
                                                    (23 reviews)
                                                    avg/night
                                                    Favorite
                                                      Viewed 8 times in the last 48 hours
                                                      16
                                                      Wonderful! 4.8/5
                                                      (16 reviews)
                                                      avg/night
                                                      Favorite
                                                        Viewed 23 times in the last 48 hours
                                                        39
                                                        Excellent! 4.7/5
                                                        (39 reviews)
                                                        avg/night
                                                        Favorite
                                                          Viewed 22 times in the last 48 hours
                                                          23
                                                          Wonderful! 4.9/5
                                                          (23 reviews)
                                                          avg/night
                                                          Favorite
                                                            Viewed 12 times in the last 48 hours
                                                            19
                                                            Wonderful! 4.9/5
                                                            (19 reviews)
                                                            avg/night
                                                            Favorite
                                                              15
                                                              Very Good! 4.1/5
                                                              (15 reviews)
                                                              avg/night
                                                              Favorite
                                                                Viewed 52 times in the last 48 hours
                                                                28
                                                                Wonderful! 4.9/5
                                                                (28 reviews)
                                                                avg/night
                                                                Favorite
                                                                  Viewed 15 times in the last 48 hours
                                                                  21
                                                                  Excellent! 4.7/5
                                                                  (21 reviews)
                                                                  avg/night
                                                                  Favorite
                                                                    Viewed 11 times in the last 48 hours
                                                                    29
                                                                    Exceptional! 5/5
                                                                    (29 reviews)
                                                                    avg/night
                                                                    Favorite
                                                                      Viewed 38 times in the last 48 hours
                                                                      19
                                                                      Exceptional! 5/5
                                                                      (19 reviews)
                                                                      avg/night
                                                                      Favorite
                                                                        6
                                                                        Wonderful! 4.8/5
                                                                        (6 reviews)
                                                                        avg/night
                                                                        Favorite
                                                                          Viewed 24 times in the last 48 hours
                                                                          9
                                                                          Exceptional! 5/5
                                                                          (9 reviews)
                                                                          avg/night
                                                                          Favorite
                                                                            7
                                                                            Excellent! 4.7/5
                                                                            (7 reviews)
                                                                            avg/night
                                                                            Favorite
                                                                              Viewed 30 times in the last 48 hours
                                                                              21
                                                                              Exceptional! 5/5
                                                                              (21 reviews)
                                                                              avg/night
                                                                              Favorite
                                                                                Viewed 29 times in the last 48 hours
                                                                                27
                                                                                Excellent! 4.7/5
                                                                                (27 reviews)
                                                                                avg/night
                                                                                Favorite
                                                                                  Viewed 22 times in the last 48 hours
                                                                                  38
                                                                                  Wonderful! 4.8/5
                                                                                  (38 reviews)
                                                                                  avg/night
                                                                                  Favorite
                                                                                    Viewed 13 times in the last 48 hours
                                                                                    33
                                                                                    Wonderful! 4.8/5
                                                                                    (33 reviews)
                                                                                    avg/night
                                                                                    Favorite
                                                                                      Viewed 28 times in the last 48 hours
                                                                                      9
                                                                                      Excellent! 4.3/5
                                                                                      (9 reviews)
                                                                                      avg/night
                                                                                      Favorite
                                                                                        Viewed 11 times in the last 48 hours
                                                                                        16
                                                                                        Excellent! 4.6/5
                                                                                        (16 reviews)
                                                                                        avg/night
                                                                                        Favorite
                                                                                          Viewed 11 times in the last 48 hours
                                                                                          16
                                                                                          Exceptional! 5/5
                                                                                          (16 reviews)
                                                                                          avg/night
                                                                                          Favorite
                                                                                            Viewed 12 times in the last 48 hours
                                                                                            14
                                                                                            Wonderful! 4.9/5
                                                                                            (14 reviews)
                                                                                            avg/night
                                                                                            Favorite
                                                                                              Viewed 8 times in the last 48 hours
                                                                                              8
                                                                                              Exceptional! 5/5
                                                                                              (8 reviews)
                                                                                              avg/night
                                                                                              Favorite
                                                                                                Viewed 65 times in the last 48 hours
                                                                                                23
                                                                                                Wonderful! 4.8/5
                                                                                                (23 reviews)
                                                                                                avg/night
                                                                                                Favorite
                                                                                                  Viewed 30 times in the last 48 hours
                                                                                                  28
                                                                                                  Wonderful! 4.9/5
                                                                                                  (28 reviews)
                                                                                                  avg/night
                                                                                                  Favorite
                                                                                                    Viewed 9 times in the last 48 hours
                                                                                                    17
                                                                                                    Exceptional! 5/5
                                                                                                    (17 reviews)
                                                                                                    avg/night
                                                                                                    Favorite
                                                                                                      Viewed 15 times in the last 48 hours
                                                                                                      30
                                                                                                      Excellent! 4.6/5
                                                                                                      (30 reviews)
                                                                                                      avg/night
                                                                                                       

                                                                                                      Recent Chatham Reviews

                                                                                                      Amazing stay in the Berksires

                                                                                                      5 of 5
                                                                                                      I was looking for a very special place in the Bershires to celebrate my husband's birthday. When I came across The Playhouse my first reaction was, "This is it!" We spent 3 wonderful days enjoying this amazing property and surrounding towns nestled beneath the mountains. The house is impeccably restored to its original splendor with contemporary furnishings and atmosphere that is deserving of a feature in Architectural Digest. We decided to eat most of our meals in to soak up every moment in the unforgettable ambiance. We loved the openess, with great views of the mountains at all times of day. The Sonos sound system really added to the experience. There was just two of us, but with a larger group this house couldn't be more perfect. We really enjoyed the scenic walk past Lake Laurel. The kitchen was amazingly equipped and the entire house from top to bottom was very clean and crisp. The exercise nook downstairs was a nice touch, too. Can't say enough about The Playhouse. Thank you Daniel for sharing this treasure!
                                                                                                      • Submitted: Oct 19, 2017
                                                                                                      • Stayed: Oct 2017

                                                                                                      perfect for our family stay

                                                                                                      4 of 5
                                                                                                      close to wedding venue, plenty of relaxation areas for everyone( indoor and out). Would have liked kitchen counters and frig more cleared(didn't like having to move others items), more specific details on departure, like unmake beds(which is what we've had to do at every other place we've stayed). Great walking to stores and eateries. Right on the main thoroughfare.
                                                                                                      • Submitted: Oct 09, 2017
                                                                                                      • Stayed: Oct 2017