check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr
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!

Windsor: Cottage Rentals (34)

  • 1 - 34 of 34
    • 2 BR
    • 1 BA
    • Sleeps 4
    14
      • 2 BR
      • 1 BA
      • Sleeps 4
      11
        • 2 BR
        • 1 BA
        • Sleeps 4
        3
          • 2 BR
          • 1 BA
          • Sleeps 6
          17
            • 3 BR
            • 1 BA
            • Sleeps 5
              • 1 BR
              • 1 BA
              • Sleeps 4
              16
                • 2 BR
                • 1 BA
                • Sleeps 6
                12
                  • 3 BR
                  • 2 BA
                  • Sleeps 6
                    • 2 BR
                    • 2 BA
                    • Sleeps 6
                    4
                      • 2 BR
                      • 1 BA
                      • Sleeps 6
                      16
                        • 3 BR
                        • 1 BA
                        • Sleeps 6
                        6
                          • 2 BR
                          • 1 BA
                          • 1 HF BA
                          • Sleeps 6
                            • 3 BR
                            • 1 BA
                            • Sleeps 4
                            1 Review
                              • 2 BR
                              • 1 BA
                              • Sleeps 7
                              3
                                • 3 BR
                                • 1 BA
                                • Sleeps 6
                                12
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 6
                                  7
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 6
                                    8
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 6
                                      33
                                        • 2 BR
                                        • 1 BA
                                        • Sleeps 6
                                        15
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 4
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 8
                                            6
                                              • 2 BR
                                              • 1 BA
                                              • Sleeps 4
                                              2 Reviews
                                                • 1 BR
                                                • 1 BA
                                                • Sleeps 2
                                                3
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                    • 3 BR
                                                    • 1 BA
                                                    • Sleeps 7
                                                    1 Review
                                                      • 3 BR
                                                      • 1 BA
                                                      • Sleeps 4
                                                        • 3 BR
                                                        • 1 BA
                                                        • 1 HF BA
                                                        • Sleeps 7
                                                        8
                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 6
                                                          4
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 8
                                                            2 Reviews
                                                              • 3 BR
                                                              • 1 BA
                                                              • 1 HF BA
                                                              • Sleeps 6
                                                                • 2 BR
                                                                • 1 BA
                                                                • 1 HF BA
                                                                • Sleeps 4
                                                                10
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 6
                                                                  10
                                                                    • 2 BR
                                                                    • 1 BA
                                                                    • Sleeps 4
                                                                    11
                                                                      View details for price
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 5
                                                                      • 1 - 34 of 34
                                                                       

                                                                      Recent Windsor Reviews

                                                                      Late summer respite...

                                                                      5 of 5
                                                                      The Clearing is just that--a space of breathtaking quiet. It is also spectacularly beautiful. My husband and I spent a week in this meticulously designed (and incredibly clean and comfortable) cabin. While we spent most of our time away--going to Arrowhead and Tanglewood and the Emily Dickinson museum--the time we spent on the screened-in porch, in the pool, and roaming the surrounding green was invaluable. The region also abounds in hiking opportunities: we went to the Savoy Mountain State Forest, the DAR State Forest, the Canoe Meadows Wildlife Sanctuary, Notchview Reservation, and the old-growth forest trail at the William Cullen Bryant homestead, which is a stone's throw from the cabin--also in Cummington. Next to the WCB homestead is also the local creamery, which has really delicious food, local beers, and home-made ice cream--all of which we enjoyed amply! John and Joyce are generous hosts, and we wanted for nothing.
                                                                      • Submitted: Aug 30, 2016
                                                                      • Stayed: Aug 2016

                                                                      It's a no brainier! This is a gem in the woods!

                                                                      5 of 5
                                                                      We love this cabin! This is such a great little retreat in the woods. It's private, quiet, and peaceful. We love the upper sitting area with the record player and full length Windows that over look the pines. Having a full kitchen and grill is a great way to stay in and enjoy the house. I suggest eating on the deck or enjoy a morning cup of coffee on the deck is quiet and relaxing. Beautiful trails at the Audubon and Kennedy park are right down the street, and when you're done for the day you can soak in the spacious hot tub or nap in the hammock. It's a great little spot that's unique and welcoming. The beds are amazingly comfortable and waking up with all the windows brings the outdoors inside. We can't wait to come back!!
                                                                      • Submitted: Aug 29, 2016
                                                                      • Stayed: Aug 2016

                                                                      Secluded but close to local towns

                                                                      5 of 5
                                                                      A comfortable, nicely maintained 2 bed home 10 min off the main road. The house has everything you could need and is centrally located for North Berkshire exploration. The owner, Valerie, stopped by to insure we had everything we needed. The only thing missing is wifi. Combine that with spotty cell service be prepared to be off the tech grid for your stay. We'd definitely stay here again when in the area.
                                                                      • Submitted: Aug 29, 2016
                                                                      • Stayed: Aug 2016