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: House Rentals (288)

  • 1 - 50 of 288
Additional fees apply. Taxes may be added.
    • 5 BR
    • 3 BA
    • Sleeps 7
      • 4 BR
      • 3 BA
      • Sleeps 8
      2 Reviews
        Excellent! 4.4/5
        (23 reviews)
        avg/night
        • 2 BR
        • 1 BA
        • Sleeps 6
        23
          • 4 BR
          • 3 BA
          • Sleeps 8
          1 Review
            • 4 BR
            • 3 BA
            • Sleeps 8
              • 4 BR
              • 2 BA
              • Sleeps 7
              3
                • 3 BR
                • 2 BA
                • Sleeps 6
                10
                  Excellent! 4.7/5
                  (10 reviews)
                  avg/night
                  • 4 BR
                  • 1 BA
                  • 1 HF BA
                  • Sleeps 8
                  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
                          • 4 BR
                          • 1 BA
                          • 1 HF BA
                          • Sleeps 9
                          10
                            • 6 BR
                            • 6 BA
                            • 1 HF BA
                            • Sleeps 14
                            1 Review
                              • 3 BR
                              • 1 BA
                              • Sleeps 8
                              3
                                • 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
                                          • 4 BR
                                          • 4 BA
                                          • 1 HF BA
                                          • Sleeps 8
                                          1 Review
                                            • 3 BR
                                            • 4 BA
                                            • Sleeps 6
                                              NEW!
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 6
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 6
                                                  Wonderful! 4.8/5
                                                  (27 reviews)
                                                  avg/night
                                                  • 5 BR
                                                  • 3 BA
                                                  • Sleeps 12
                                                  27
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    1 Review
                                                      Exceptional! 5.0/5
                                                      (6 reviews)
                                                      avg/night
                                                      • 3 BR
                                                      • 2 BA
                                                      • 1 HF BA
                                                      • Sleeps 6
                                                      6
                                                        Wonderful! 4.8/5
                                                        (15 reviews)
                                                        avg/night
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 10
                                                        15
                                                          Exceptional! 5.0/5
                                                          (7 reviews)
                                                          avg/night
                                                          • 3 BR
                                                          • 2 BA
                                                          • 1 HF BA
                                                          • Sleeps 8
                                                          7
                                                            • 3 BR
                                                            • 2 BA
                                                            • 1 HF BA
                                                            • Sleeps 6
                                                              • 4 BR
                                                              • 3 BA
                                                              • Sleeps 8
                                                              34
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 5
                                                                  • 5 BR
                                                                  • 3 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 16
                                                                  3
                                                                    • 2 BR
                                                                    • 1 BA
                                                                    • Sleeps 4
                                                                    4
                                                                      Excellent! 4.7/5
                                                                      (9 reviews)
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 8
                                                                      9
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 7
                                                                        4
                                                                          • 3 BR
                                                                          • 3 BA
                                                                          • Sleeps 6
                                                                          8
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 8
                                                                            6
                                                                              Excellent! 4.7/5
                                                                              (14 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 5
                                                                              14
                                                                                • 4 BR
                                                                                • 3 BA
                                                                                • Sleeps 8
                                                                                2 Reviews
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 8
                                                                                  25
                                                                                    • 4 BR
                                                                                    • 1 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 8
                                                                                    6
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 6
                                                                                      1 Review
                                                                                        Exceptional! 5.0/5
                                                                                        (7 reviews)
                                                                                        avg/night
                                                                                        • 4 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 7
                                                                                        7
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 4
                                                                                          26
                                                                                            Wonderful! 4.8/5
                                                                                            (17 reviews)
                                                                                            avg/night
                                                                                            • 3 BR
                                                                                            • 3 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 10
                                                                                            17
                                                                                              Wonderful! 4.9/5
                                                                                              (11 reviews)
                                                                                              avg/night
                                                                                              • 4 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 8
                                                                                              11
                                                                                                NEW!
                                                                                                Wonderful! 4.8/5
                                                                                                (5 reviews)
                                                                                                avg/night
                                                                                                • 2 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                5
                                                                                                  • 4 BR
                                                                                                  • 2 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 10
                                                                                                  3
                                                                                                    • 4 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 7
                                                                                                    11
                                                                                                    • 1 - 50 of 288
                                                                                                     

                                                                                                    Recent Monterey Reviews

                                                                                                    Beautiful Berkshire Location

                                                                                                    5 of 5
                                                                                                    The Schoolhouse is a beautiful home w. everything you could possibly need for your vacation. A quiet location, close to town and many Berkshire attractions. Super spacious and family friendly.
                                                                                                    • Submitted: Sep 19, 2016
                                                                                                    • Stayed: Sep 2016

                                                                                                    What a wonderful experience!

                                                                                                    5 of 5
                                                                                                    Beautiful home, amazing amenities, everything and anything we needed! Flawless check-in and check-out. Power outage on the last day but the hosts immediately checked in with us and updated us on the situation. Clean, comfortable, and on an amazing property, explored the pond and many places in Berkshire County! Highly recommend this house and host, thank you for a wonderful mini-vacation!
                                                                                                    • Submitted: Sep 11, 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