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!

Winchester: Apartments, Houses & More (1,089)

  • 1 - 50 of 1,089
Additional fees apply. Taxes may be added.
    • 6 BR
    • 4 BA
    • 1 HF BA
    • Sleeps 16
    15
      NEW!
      • 4 BR
      • 2 BA
      • Sleeps 7
        NEW!
        • 2 BR
        • 2 BA
        • Sleeps 6
          • Studio
          • 1 BA
          • Sleeps 2
            • 3 BR
            • 1 BA
            • Sleeps 6
            87
              NEW!
              • 2 BR
              • 2 BA
              • Sleeps 7
              1 Review
                NEW!
                • 3 BR
                • 1 BA
                • Sleeps 5
                  • 3 BR
                  • 2 BA
                  • Sleeps 6
                  4
                    NEW!
                    • 2 BR
                    • 2 BA
                    • Sleeps 5
                      NEW!
                      • Studio
                      • 1 BA
                      • Sleeps 2
                        NEW!
                        • 2 BR
                        • 1 BA
                        • Sleeps 4
                          NEW!
                          • 3 BR
                          • 1 BA
                          • Sleeps 6
                          4
                            • 1 BR
                            • 1 BA
                            • Sleeps 4
                              NEW!
                                NEW!
                                • Studio
                                • 2 BA
                                • Sleeps 5
                                  NEW!
                                  • Studio
                                  • 2 BA
                                  • Sleeps 5
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 4
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 4
                                      5
                                        NEW!
                                        • 5 BR
                                        • 6 BA
                                        • Sleeps 10
                                          NEW!
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 4
                                            NEW!
                                            • 3 BR
                                            • 1 BA
                                            • Sleeps 6
                                              NEW!
                                              • 3 BR
                                              • 1 BA
                                              • Sleeps 7
                                                NEW!
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 9
                                                  NEW!
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 9
                                                    NEW!
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                      NEW!
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 8
                                                        NEW!
                                                        • 2 BR
                                                        • 2 BA
                                                        • Sleeps 4
                                                          NEW!
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 4
                                                            NEW!
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 4
                                                              NEW!
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 2
                                                                NEW!
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 2
                                                                  NEW!
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 4
                                                                    NEW!
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 1
                                                                      NEW!
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 1
                                                                        NEW!
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 2
                                                                          NEW!
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 5
                                                                          3
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 6
                                                                            2 Reviews
                                                                              NEW!
                                                                              • 4 BR
                                                                              • 2 BA
                                                                              • Sleeps 8
                                                                                • 3 BR
                                                                                • Sleeps 5
                                                                                  NEW!
                                                                                  • 3 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 8
                                                                                    • 1 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 2
                                                                                    6
                                                                                      • Studio
                                                                                      • 1 BA
                                                                                      • Sleeps 4
                                                                                      9
                                                                                        NEW!
                                                                                        • 4 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 6
                                                                                        1 Review
                                                                                          NEW!
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                            • Studio
                                                                                            • 1 BA
                                                                                            • Sleeps 2
                                                                                            13
                                                                                              NEW!
                                                                                              View details for price
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              1 Review
                                                                                                • Studio
                                                                                                • 1 BA
                                                                                                • Sleeps 2
                                                                                                14
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  13
                                                                                                    NEW!
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 2
                                                                                                      NEW!
                                                                                                      • 2 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 4
                                                                                                      • 1 - 50 of 1,089
                                                                                                       

                                                                                                      Recent Winchester Reviews

                                                                                                      Wonderful, warm, welcoming. Highly recommended

                                                                                                      5 of 5
                                                                                                      Thank you! This space was so welcoming and homey. We were all so grateful for a comfortable place to relax and spend time together after fun-packed days exploring Boston and Cambridge. The extra special touches were wonderful. The location was great as well. We HIGHLY recommend this property! Thanks for your hospitality.
                                                                                                      • Submitted: Aug 11, 2016
                                                                                                      • Stayed: Jul 2016

                                                                                                      Multi generational family vacation

                                                                                                      5 of 5
                                                                                                      The Dougherty home in Winchester Massachusetts was very comfortable. It was a very close, comfortable distance to Boston. Only 13 miles to Logan international. We also drove to Plymouth and Salem. The home is located close to the freeway system, however, you would never know it when relaxing in their backyard at the end of a busy day. We would definitely recommend their home for a large family or anyone that wants more room to visit and relax in. The murphys from Northern California
                                                                                                      • Submitted: Aug 10, 2016
                                                                                                      • Stayed: Jul 2016

                                                                                                      Nice air B&B located in a safe and friendly family neighborhood

                                                                                                      5 of 5
                                                                                                      My husband and I enjoyed staying at this air B&B. Mont was on a trip during our stay but was easily contacted when needed. Mont's home is very comfortable, clean, and cozy. The listing of suggestions he sent to us before our arrival were helpful to us during our week's stay. The location of this home is good. There is easy access to Boston with public transportation a few walking minutes away. Upon our arrival, we discovered that there was no air conditioning. Mont assured us that we would be comfortable with the fans running and screened windows left open. This was the case. We would indeed recommend this property to friends or relatives visiting Boston and surrounding areas.
                                                                                                      • Submitted: Aug 6, 2016
                                                                                                      • Stayed: Jul 2016