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
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Monterey: Houses, Cottages & More (139)

  • 1 - 50 of 139
Additional fees apply. Taxes may be added.
    Excellent! 4.7/5
    (6 reviews)
    avg/night
    • 2 BR
    • 1 BA
    • Sleeps 4
    6
      • 4 BR
      • 2 BA
      • 1 HF BA
      • Sleeps 8
      6
        • 5 BR
        • 3 BA
        • Sleeps 7
          • 4 BR
          • 2 BA
          • Sleeps 7
          3
            • 4 BR
            • 3 BA
            • Sleeps 8
            2 Reviews
              Excellent! 4.7/5
              (10 reviews)
              avg/night
              • 4 BR
              • 1 BA
              • 1 HF BA
              • Sleeps 8
              10
                • 3 BR
                • 1 BA
                • Sleeps 6
                12
                  Excellent! 4.4/5
                  (23 reviews)
                  avg/night
                  • 2 BR
                  • 1 BA
                  • Sleeps 6
                  23
                    • 2 BR
                    • 1 BA
                    • Sleeps 5
                    3
                      • 4 BR
                      • 3 BA
                      • Sleeps 8
                      1 Review
                        • 4 BR
                        • 3 BA
                        • Sleeps 8
                          • 3 BR
                          • 2 BA
                          • Sleeps 6
                          10
                            Exceptional! 5.0/5
                            (12 reviews)
                            avg/night
                            • 3 BR
                            • 3 BA
                            • Sleeps 9
                            12
                              • 5 BR
                              • 2 BA
                              • 1 HF BA
                              • Sleeps 12
                              9
                                Wonderful! 4.8/5
                                (13 reviews)
                                avg/night
                                • 5 BR
                                • 2 BA
                                • 1 HF BA
                                • Sleeps 12
                                13
                                  Excellent! 4.7/5
                                  (11 reviews)
                                  avg/night
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 4
                                  11
                                    • 4 BR
                                    • 1 BA
                                    • 1 HF BA
                                    • Sleeps 9
                                    10
                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 10
                                      6
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 4
                                          • 6 BR
                                          • 6 BA
                                          • 1 HF BA
                                          • Sleeps 14
                                          1 Review
                                            • 3 BR
                                            • 1 BA
                                            • Sleeps 8
                                            3
                                              • 2 BR
                                              • 1 BA
                                              • Sleeps 6
                                              6
                                                • 4 BR
                                                • 3 BA
                                                • Sleeps 12
                                                2 Reviews
                                                  • 3 BR
                                                  • 2 BA
                                                  • 1 HF BA
                                                  • Sleeps 8
                                                  2 Reviews
                                                    • 6 BR
                                                    • 3 BA
                                                    • Sleeps 12
                                                    13
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 8
                                                        Excellent! 4.7/5
                                                        (10 reviews)
                                                        avg/night
                                                        • 5 BR
                                                        • 2 BA
                                                        • Sleeps 8
                                                        10
                                                          • 6 BR
                                                          • 4 BA
                                                          • Sleeps 12
                                                          2 Reviews
                                                            • 2 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            4
                                                              • 4 BR
                                                              • 4 BA
                                                              • 1 HF BA
                                                              • Sleeps 8
                                                              1 Review
                                                                • 2 BR
                                                                • 1 BA
                                                                • 1 HF BA
                                                                • Sleeps 6
                                                                10
                                                                  Wonderful! 4.9/5
                                                                  (14 reviews)
                                                                  avg/night
                                                                  • 4 BR
                                                                  • 2 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 7
                                                                  14
                                                                    NEW!
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                      • 3 BR
                                                                      • 4 BA
                                                                      • Sleeps 6
                                                                        • 3 BR
                                                                        • 3 BA
                                                                        • Sleeps 6
                                                                          NEW!
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 6
                                                                              • 4 BR
                                                                              • 2 BA
                                                                              • Sleeps 10
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 8
                                                                                1 Review
                                                                                  Wonderful! 4.8/5
                                                                                  (6 reviews)
                                                                                  avg/night
                                                                                  • 4 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 10
                                                                                  6
                                                                                    • 5 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 10
                                                                                      Wonderful! 4.8/5
                                                                                      (27 reviews)
                                                                                      avg/night
                                                                                      • 5 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 12
                                                                                      27
                                                                                        Wonderful! 4.9/5
                                                                                        (16 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 5
                                                                                        16
                                                                                          Excellent! 4.7/5
                                                                                          (22 reviews)
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 5
                                                                                          22
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 6
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 6
                                                                                              1 Review
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 8
                                                                                                4
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                    • 4 BR
                                                                                                    • 3 BA
                                                                                                    • 1 HF BA
                                                                                                    • Sleeps 10
                                                                                                      • 3 BR
                                                                                                      • 1 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 5
                                                                                                      8
                                                                                                      • 1 - 50 of 139
                                                                                                       

                                                                                                      Recent Monterey Reviews

                                                                                                      Perfect getaway

                                                                                                      5 of 5
                                                                                                      This is our 3rd time returning to the schoolhouse cottage and we plan to continue the yearly tradition. The cottage is clean, spacious and feels like a home away from home. Nestled up against wooded property it is quiet and peaceful yet a few minutes drive to the center of town. Excellent restaurants, shopping and hiking nearby. Our host is more than welcoming every year and we look forward to our return trip.
                                                                                                      • Submitted: Sep 19, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      Perfect Weekend

                                                                                                      5 of 5
                                                                                                      This cottage is exactly as described. Very clean. Super cute. We were four people and each of us managed to have our own space at night with a futon in both the living room and sun room, and then a queen bed in one bedroom, and two twins in another. It's located just over the hill from the lake. Just a two minute walk. We had so much fun hanging out on the dock and paddling around the lake in the canoe. In the local surrounding area we went apple picking, did a wine tasting, bought fresh raspberries by the side of the road, hiked some neighboring trails. The location is also very convenient to Great Barrington for restaurants and groceries. As some of the other comments mentioned, the bedroom walls don't reach the ceiling, so if you're a light sleeper, it might be tough as you can hear everything going on anywhere in the cottage. It didn't bother us one bit and we learned that this is the style of other lake houses in the area. Would rent this place again in a heartbeat. The owners were incredibly responsive, helpful, and kind. A+
                                                                                                      • Submitted: Sep 8, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      The house was very comfortable& the view of the lake was wonderful from both the sun room & the deck

                                                                                                      5 of 5
                                                                                                      We enjoyed the house very much. It was a family gathering & everyone found wonderful things to do without even leaving the property. We barbecued, enjoyed the huge, shady deck, & the lake. Our sons went fishing & kayaking, we enjoyed the large raft & our 3 year old granddaughter loved finding snail shells & watching the fish in the lake. We also took her to nearby Lake Garfield one day. It is a free public beach & she loved playing in the sand & being with other kids. Eric was an excellent host. He responded very quickly when we texted him a couple of times with questions. The kitchen was well stocked. We were 6 adults & we fit very comfortably into the living room at night. Thank you, Eric!
                                                                                                      • Submitted: Sep 6, 2016
                                                                                                      • Stayed: Aug 2016