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  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
    Excellent! 4.6/5
    (11 reviews)
    avg/night
    • 4 BR
    • 1 BA
    • 1 HF BA
    • Sleeps 8
    House #467696vb
    11
      • 5 BR
      • 3 BA
      • Sleeps 7
      House #399933vb
        • 3 BR
        • 2 BA
        • Sleeps 6
        House #233555vb
        10
          Wonderful! 4.8/5
          (13 reviews)
          avg/night
          • 5 BR
          • 2 BA
          • 1 HF BA
          • Sleeps 12
          House #561543vb
          13
          Viewed 12 times in the last 48 hours
            Exceptional! 5.0/5
            (12 reviews)
            avg/night
            • 3 BR
            • 3 BA
            • Sleeps 9
            House #593614vb
            12
            Viewed 19 times in the last 48 hours
              Wonderful! 4.8/5
              (6 reviews)
              avg/night
              • 4 BR
              • 2 BA
              • Sleeps 10
              Chalet #793621vb
              6
              Viewed 7 times in the last 48 hours
                avg/night
                • 3 BR
                • 2 BA
                • 1 HF BA
                • Sleeps 8
                House #590505vb
                2
                Viewed 15 times in the last 48 hours
                  avg/night
                  • 3 BR
                  • 1 BA
                  • Sleeps 8
                  House #833424vb
                  3
                  Viewed 7 times in the last 48 hours
                    • 3 BR
                    • 2 BA
                    • Sleeps 8
                    House #863717vb
                    Viewed 7 times in the last 48 hours
                      • 4 BR
                      • 3 BA
                      • Sleeps 8
                      House #788022vb
                      2
                        • 3 BR
                        • 2 BA
                        • Sleeps 6
                        House #921303vb
                          Excellent! 4.7/5
                          (10 reviews)
                          avg/night
                          • 5 BR
                          • 2 BA
                          • Sleeps 8
                          House #349905vb
                          10
                            • 4 BR
                            • 4 BA
                            • 1 HF BA
                            • Sleeps 8
                            House #874227vb
                            1
                            Viewed 5 times in the last 48 hours
                              Wonderful! 4.9/5
                              (14 reviews)
                              avg/night
                              • 4 BR
                              • 2 BA
                              • 1 HF BA
                              • Sleeps 7
                              Cottage #3023396
                              14
                              Viewed 10 times in the last 48 hours
                                avg/night
                                • 3 BR
                                • 2 BA
                                • Sleeps 6
                                Chateau / Country House #908959vb
                                1
                                Viewed 15 times in the last 48 hours
                                  avg/night
                                  • 3 BR
                                  • 4 BA
                                  • Sleeps 6
                                  House #3960887
                                  Viewed 16 times in the last 48 hours
                                    • 4 BR
                                    • 3 BA
                                    • Sleeps 8
                                    House #227099
                                    9
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 6
                                      Chalet #480749vb
                                      6
                                        • 3 BR
                                        • 3 BA
                                        • Sleeps 6
                                        Farmhouse #873131vb
                                          • 5 BR
                                          • 5 BA
                                          • Sleeps 12
                                          House #3632142
                                            • 5 BR
                                            • 2 BA
                                            • Sleeps 8
                                            House #123410
                                            4
                                              • 4 BR
                                              • 3 BA
                                              • Sleeps 8
                                              House #143111vb
                                                • 4 BR
                                                • 2 BA
                                                • Sleeps 7
                                                House #774024vb
                                                4
                                                Viewed 10 times in the last 48 hours
                                                  Exceptional! 5.0/5
                                                  (11 reviews)
                                                  avg/night
                                                  • 5 BR
                                                  • 2 BA
                                                  • 1 HF BA
                                                  • Sleeps 12
                                                  House #621016vb
                                                  11
                                                  Viewed 25 times in the last 48 hours
                                                    • 6 BR
                                                    • 6 BA
                                                    • 1 HF BA
                                                    • Sleeps 14
                                                    House #3540891
                                                    4
                                                    Viewed 8 times in the last 48 hours
                                                      Exceptional! 5.0/5
                                                      (12 reviews)
                                                      avg/night
                                                      • 3 BR
                                                      • 1 BA
                                                      • Sleeps 6
                                                      Cottage #513698vb
                                                      12
                                                      Viewed 13 times in the last 48 hours
                                                        Exceptional! 5.0/5
                                                        (10 reviews)
                                                        avg/night
                                                        • 4 BR
                                                        • 1 BA
                                                        • 1 HF BA
                                                        • Sleeps 9
                                                        House #4154013
                                                        10
                                                        Viewed 13 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (18 reviews)
                                                          avg/night
                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 5
                                                          Cottage #707780vb
                                                          18
                                                          Viewed 7 times in the last 48 hours
                                                            avg/night
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 8
                                                            House #929167vb
                                                            Viewed 8 times in the last 48 hours
                                                              Wonderful! 4.8/5
                                                              (12 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 1 BA
                                                              • Sleeps 4
                                                              Cabin #556947vb
                                                              12
                                                              Viewed 11 times in the last 48 hours
                                                                Excellent! 4.3/5
                                                                (7 reviews)
                                                                avg/night
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                Cottage #7114544
                                                                7
                                                                  Wonderful! 4.8/5
                                                                  (27 reviews)
                                                                  avg/night
                                                                  • 5 BR
                                                                  • 3 BA
                                                                  • Sleeps 12
                                                                  House #424518vb
                                                                  27
                                                                  Viewed 22 times in the last 48 hours
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 4
                                                                    Cottage #4142288
                                                                      avg/night
                                                                      • 4 BR
                                                                      • 3 BA
                                                                      • Sleeps 12
                                                                      House #788340vb
                                                                      2
                                                                      Viewed 6 times in the last 48 hours
                                                                        Wonderful! 4.8/5
                                                                        (5 reviews)
                                                                        avg/night
                                                                        • 2 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                        Cottage #3953792
                                                                        5
                                                                        Viewed 8 times in the last 48 hours
                                                                          Excellent! 4.7/5
                                                                          (23 reviews)
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 5
                                                                          Cottage #3624808
                                                                          23
                                                                          Viewed 10 times in the last 48 hours
                                                                            Excellent! 4.7/5
                                                                            (15 reviews)
                                                                            avg/night
                                                                            • 1 BR
                                                                            • 2 BA
                                                                            • Sleeps 4
                                                                            Chalet #384598vb
                                                                            15
                                                                            Viewed 17 times in the last 48 hours
                                                                              Wonderful! 4.9/5
                                                                              (13 reviews)
                                                                              avg/night
                                                                              • 6 BR
                                                                              • 3 BA
                                                                              • Sleeps 12
                                                                              House #559190vb
                                                                              13
                                                                              Viewed 10 times in the last 48 hours
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 8
                                                                                Cabin #563653vb
                                                                                2
                                                                                  avg/night
                                                                                  • 5 BR
                                                                                  • 4 BA
                                                                                  • 2 HF BA
                                                                                  • Sleeps 10
                                                                                  Estate #558988vb
                                                                                  4
                                                                                  Viewed 6 times in the last 48 hours
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                    House #3897254
                                                                                    4
                                                                                      Excellent! 4.7/5
                                                                                      (11 reviews)
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 8
                                                                                      House #607741vb
                                                                                      11
                                                                                      Viewed 12 times in the last 48 hours
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 6
                                                                                        Cottage #183642
                                                                                        10
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          House #830744vb
                                                                                          3
                                                                                          Viewed 9 times in the last 48 hours
                                                                                            • 4 BR
                                                                                            • 3 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 10
                                                                                            House #820818vb
                                                                                            Viewed 5 times in the last 48 hours
                                                                                              Exceptional! 5.0/5
                                                                                              (5 reviews)
                                                                                              avg/night
                                                                                              • 5 BR
                                                                                              • 3 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 16
                                                                                              House #866131vb
                                                                                              5
                                                                                              Viewed 11 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (11 reviews)
                                                                                                avg/night
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 4
                                                                                                Cottage #214201
                                                                                                11
                                                                                                Viewed 6 times in the last 48 hours
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 8
                                                                                                  Bungalow #717959vb
                                                                                                  5
                                                                                                    • 5 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 10
                                                                                                    Lodge #487322vb
                                                                                                    3
                                                                                                      Exceptional! 5.0/5
                                                                                                      (8 reviews)
                                                                                                      avg/night
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 6
                                                                                                      House #4153058
                                                                                                      8
                                                                                                      • 1 - 50 of 300+

                                                                                                      Monterey: Houses, Cottages & More (300+)

                                                                                                       

                                                                                                      Recent Monterey Reviews

                                                                                                      Just What We Needed!

                                                                                                      5 of 5
                                                                                                      Doug was an amazing host. We had a large group of friends staying to attend a wedding close by at Gedney Farm. The house accommodated us perfectly. We loved that every room has its own bathroom. The house itself is spacious and in my opinion looks better in person! Thank you to Doug for being so helpful and hospitable. I would absolutely recommend staying here to anyone looking to have a very pleasant stay in a lovely HISTORIC home!
                                                                                                      • Submitted: Nov 11, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Lovely home

                                                                                                      5 of 5
                                                                                                      Very thoughtfully appointed, comfortable, clean, private and well-situated cottage perfect for a weekend in the Berkshires. Thanks for all the thoughtful touches that made it such a cozy place to stay!
                                                                                                      • Submitted: Oct 31, 2016
                                                                                                      • Stayed: Oct 2016

                                                                                                      Annual Fall Mem

                                                                                                      4 of 5
                                                                                                      We had a fabulous weekend and the place held the six of us perfectly. Truly appreciated the kitchen and living-dining room space for gathering and group conversations. Liked that it was separated from the TV room where the sports fans could be by themselves. We ended up hiking several sections of the Appalachian trail on Friday, Saturday and Sunday. 24 miles total. Feeling pretty lame today!
                                                                                                      • Submitted: Oct 27, 2016
                                                                                                      • Stayed: Oct 2016