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
  • Showing 1-50 of 300+
  View map Map
Additional fees apply. Taxes may be added.
Favorite
    Viewed 7 times in the last 48 hours
    • 5 bedrooms
    • 2 bathrooms
    • 1 HF BA
    • Sleeps 12
    Favorite
      Viewed 27 times in the last 48 hours
      • 4 bedrooms
      • 1 bathroom
      • 1 HF BA
      • Sleeps 8
      Favorite
        Viewed 26 times in the last 48 hours
        • 4 bedrooms
        • 3 bathrooms
        • Sleeps 8
        Favorite
          Viewed 27 times in the last 48 hours
          • 4 bedrooms
          • 2 bathrooms
          • Sleeps 10
          Favorite
            Viewed 8 times in the last 48 hours
            • 2 bedrooms
            • 1 bathroom
            • Sleeps 6
            Favorite
              Viewed 8 times in the last 48 hours
              • 3 bedrooms
              • 2 bathrooms
              • Sleeps 6
              Favorite
                Favorite
                  Viewed 11 times in the last 48 hours
                  • 2 bedrooms
                  • 1 bathroom
                  • Sleeps 5
                  Favorite
                    Viewed 5 times in the last 48 hours
                    • 3 bedrooms
                    • 3 bathrooms
                    • Sleeps 9
                    Favorite
                      Viewed 9 times in the last 48 hours
                      • 3 bedrooms
                      • 1 bathroom
                      • Sleeps 8
                      Favorite
                        • 5 bedrooms
                        • 2 bathrooms
                        • Sleeps 8
                        Favorite
                          Viewed 14 times in the last 48 hours
                          • 4 bedrooms
                          • 4 bathrooms
                          • 1 HF BA
                          • Sleeps 8
                          Favorite
                            Favorite
                              Viewed 22 times in the last 48 hours
                              • 3 bedrooms
                              • 2 bathrooms
                              • 1 HF BA
                              • Sleeps 8
                              Favorite
                                Viewed 11 times in the last 48 hours
                                • 3 bedrooms
                                • 4 bathrooms
                                • Sleeps 6
                                Favorite
                                  Viewed 18 times in the last 48 hours
                                  • 5 bedrooms
                                  • 2 bathrooms
                                  • Sleeps 8
                                  Favorite
                                    Viewed 12 times in the last 48 hours
                                    • 4 bedrooms
                                    • 2 bathrooms
                                    • 1 HF BA
                                    • Sleeps 7
                                    Favorite
                                      Viewed 5 times in the last 48 hours
                                      • 3 bedrooms
                                      • 3 bathrooms
                                      • Sleeps 6
                                      Favorite
                                        Favorite
                                          • 4 bedrooms
                                          • 3 bathrooms
                                          • Sleeps 10
                                          Favorite
                                            Viewed 6 times in the last 48 hours
                                            • 4 bedrooms
                                            • 3 bathrooms
                                            • Sleeps 8
                                            Favorite
                                              Viewed 9 times in the last 48 hours
                                              • 4 bedrooms
                                              • 3 bathrooms
                                              • Sleeps 8
                                              Favorite
                                                Viewed 122 times in the last 48 hours
                                                • 6 bedrooms
                                                • 5 bathrooms
                                                • Sleeps 20
                                                Favorite
                                                  Viewed 11 times in the last 48 hours
                                                  • 3 bedrooms
                                                  • 2 bathrooms
                                                  • Sleeps 7
                                                  Favorite
                                                    Viewed 9 times in the last 48 hours
                                                    • 2 bedrooms
                                                    • 2 bathrooms
                                                    • Sleeps 6
                                                    Favorite
                                                      Viewed 36 times in the last 48 hours
                                                      • 3 bedrooms
                                                      • 2 bathrooms
                                                      • Sleeps 4
                                                      Favorite
                                                        Viewed 38 times in the last 48 hours
                                                        • 2 bedrooms
                                                        • 1 bathroom
                                                        • Sleeps 5
                                                        Favorite
                                                          Viewed 40 times in the last 48 hours
                                                          • 3 bedrooms
                                                          • 3 bathrooms
                                                          • Sleeps 8
                                                          Favorite
                                                            Viewed 10 times in the last 48 hours
                                                            • 4 bedrooms
                                                            • 3 bathrooms
                                                            • Sleeps 9
                                                            Favorite
                                                              Viewed 12 times in the last 48 hours
                                                              • 5 bedrooms
                                                              • 5 bathrooms
                                                              • Sleeps 12
                                                              Favorite
                                                                Viewed 16 times in the last 48 hours
                                                                • 4 bedrooms
                                                                • 2 bathrooms
                                                                • Sleeps 8
                                                                Favorite
                                                                  Viewed 5 times in the last 48 hours
                                                                  • 2 bedrooms
                                                                  • 1 bathroom
                                                                  • Sleeps 6
                                                                  Favorite
                                                                    Viewed 43 times in the last 48 hours
                                                                    • 2 bedrooms
                                                                    • 1 bathroom
                                                                    • Sleeps 4
                                                                    Favorite
                                                                      • 1 bedroom
                                                                      • 1 bathroom
                                                                      • Sleeps 3
                                                                      Favorite
                                                                        Viewed 11 times in the last 48 hours
                                                                        • 1 bedroom
                                                                        • 1 bathroom
                                                                        • Sleeps 4
                                                                        Favorite
                                                                          • 4 bedrooms
                                                                          • 2 bathrooms
                                                                          • 1 HF BA
                                                                          • Sleeps 8
                                                                          Favorite
                                                                            Viewed 42 times in the last 48 hours
                                                                            • 2 bedrooms
                                                                            • 2 bathrooms
                                                                            • Sleeps 6
                                                                            Favorite
                                                                              Viewed 11 times in the last 48 hours
                                                                              • 5 bedrooms
                                                                              • 4 bathrooms
                                                                              • 1 HF BA
                                                                              • Sleeps 12
                                                                              Favorite
                                                                                Viewed 9 times in the last 48 hours
                                                                                • 2 bedrooms
                                                                                • 2 bathrooms
                                                                                • Sleeps 8
                                                                                Favorite
                                                                                  Viewed 9 times in the last 48 hours
                                                                                  • 4 bedrooms
                                                                                  • 3 bathrooms
                                                                                  • Sleeps 8
                                                                                  Favorite
                                                                                    Viewed 30 times in the last 48 hours
                                                                                    • 5 bedrooms
                                                                                    • 2 bathrooms
                                                                                    • 1 HF BA
                                                                                    • Sleeps 10
                                                                                    Favorite
                                                                                      Viewed 19 times in the last 48 hours
                                                                                      • 3 bedrooms
                                                                                      • 3 bathrooms
                                                                                      • 1 HF BA
                                                                                      • Sleeps 10
                                                                                      Favorite
                                                                                        Viewed 5 times in the last 48 hours
                                                                                        • 3 bedrooms
                                                                                        • 2 bathrooms
                                                                                        • Sleeps 8
                                                                                        Favorite
                                                                                          Viewed 17 times in the last 48 hours
                                                                                          • 2 bedrooms
                                                                                          • 2 bathrooms
                                                                                          • Sleeps 6
                                                                                          Favorite
                                                                                            Viewed 25 times in the last 48 hours
                                                                                            • 1 bedroom
                                                                                            • 1 bathroom
                                                                                            • Sleeps 5
                                                                                            Favorite
                                                                                              Viewed 19 times in the last 48 hours
                                                                                              • 6 bedrooms
                                                                                              • 3 bathrooms
                                                                                              • Sleeps 10
                                                                                              Favorite
                                                                                                Viewed 15 times in the last 48 hours
                                                                                                • 3 bedrooms
                                                                                                • 2 bathrooms
                                                                                                • Sleeps 10
                                                                                                Favorite
                                                                                                  Viewed 44 times in the last 48 hours
                                                                                                  • 4 bedrooms
                                                                                                  • 3 bathrooms
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 12
                                                                                                  Favorite
                                                                                                    Viewed 16 times in the last 48 hours
                                                                                                    • 2 bedrooms
                                                                                                    • 1 bathroom
                                                                                                    • Sleeps 4
                                                                                                    Favorite
                                                                                                      Viewed 12 times in the last 48 hours
                                                                                                      • 5 bedrooms
                                                                                                      • 3 bathrooms
                                                                                                      • Sleeps 8
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Monterey 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

                                                                                                      Great Location, Well-Supplied, Great Stay !

                                                                                                      5 of 5
                                                                                                      My family (2 couples, 1 more adult) stayed here during most of the Christmas-New Year's week. We managed with the 2 bedrooms, 1 pullout sofa and 1 bathroom. The rental, part of a duplex, is surrounded by lovely large white pines and Norway spruces, and there's a view across the road to West Stockbridge Mountain. Stockbridge Bowl is very close but, needless to say, this wasn't the month for swimming. Carmen was very conscientious in responding to questions and checking in with us when a storm approached. In addition to the prompt snow plowing, we appreciated the supplies of dryer sheets, dish liquid, a roll of paper towels and the like. Very considerate! The kitchen is well-supplied with sturdy dishes, utensils and cooking appliances.
                                                                                                      • Submitted: Jan 10, 2017
                                                                                                      • Stayed: Dec 2016