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 svg-report-flag
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!
  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
    Exceptional! 5.0/5
    (15 reviews)
    avg/night
    • 6 BR
    • 4 BA
    • 1 HF BA
    • Sleeps 16
    House #3484286
    15
    Viewed 7 times in the last 48 hours
      avg/night
      • 4 BR
      • 2 BA
      • Sleeps 7
      House #899434vb
      1
      Viewed 33 times in the last 48 hours
        • 3 BR
        • 2 BA
        • Sleeps 6
        House #4359969
          Wonderful! 4.9/5
          (32 reviews)
          avg/night
          • 2 BR
          • 2 BA
          • Sleeps 5
          Apartment #4025774
          32
          Viewed 26 times in the last 48 hours
            Excellent! 4.7/5
            (7 reviews)
            avg/night
            • 1 BR
            • 1 BA
            • Sleeps 2
            Apartment #4102983
            7
            Viewed 17 times in the last 48 hours
              Excellent! 4.7/5
              (27 reviews)
              avg/night
              • 3 BR
              • 2 BA
              • 1 HF BA
              • Sleeps 7
              Apartment #4055099
              27
              Viewed 21 times in the last 48 hours
                Exceptional! 5.0/5
                (6 reviews)
                avg/night
                • 3 BR
                • 2 BA
                • Sleeps 6
                Cottage #4054235
                6
                Viewed 7 times in the last 48 hours
                  Excellent! 4.7/5
                  (18 reviews)
                  avg/night
                  • 2 BR
                  • 2 BA
                  • Sleeps 5
                  Apartment #4055098
                  18
                  Viewed 8 times in the last 48 hours
                    Exceptional! 5.0/5
                    (47 reviews)
                    avg/night
                    • 2 BR
                    • 1 BA
                    • Sleeps 6
                    Apartment #3928905
                    47
                    Viewed 18 times in the last 48 hours
                      Wonderful! 4.8/5
                      (47 reviews)
                      avg/night
                      • 2 BR
                      • 1 BA
                      • Sleeps 6
                      Apartment #3661758
                      47
                      Viewed 19 times in the last 48 hours
                        Excellent! 4.7/5
                        (22 reviews)
                        avg/night
                        • 2 BR
                        • 1 BA
                        • Sleeps 5
                        Apartment #4096548
                        22
                        Viewed 29 times in the last 48 hours
                          • 2 BR
                          • 1 BA
                          • Sleeps 5
                          Cottage #650215vb
                          8
                            Wonderful! 4.9/5
                            (16 reviews)
                            avg/night
                            • 4 BR
                            • 4 BA
                            • 1 HF BA
                            • Sleeps 8
                            Apartment #4061075
                            16
                            Viewed 12 times in the last 48 hours
                              Wonderful! 4.9/5
                              (17 reviews)
                              avg/night
                              • 1 BR
                              • 1 BA
                              • Sleeps 4
                              Apartment #181404
                              17
                                Wonderful! 4.9/5
                                (55 reviews)
                                avg/night
                                • 1 BR
                                • 1 BA
                                • 1 HF BA
                                • Sleeps 2
                                House #443453vb
                                55
                                Viewed 34 times in the last 48 hours
                                  Wonderful! 4.8/5
                                  (33 reviews)
                                  avg/night
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 5
                                  Cottage #176726
                                  33
                                  Viewed 6 times in the last 48 hours
                                    Excellent! 4.5/5
                                    (11 reviews)
                                    avg/night
                                    • 2 BR
                                    • 2 BA
                                    • Sleeps 5
                                    Apartment #4105862
                                    11
                                    Viewed 41 times in the last 48 hours
                                      Excellent! 4.6/5
                                      (32 reviews)
                                      avg/night
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 4
                                      Cottage #592845vb
                                      32
                                      Viewed 27 times in the last 48 hours
                                        Wonderful! 4.9/5
                                        (11 reviews)
                                        avg/night
                                        • 4 BR
                                        • 4 BA
                                        • Sleeps 8
                                        Apartment #4061076
                                        11
                                        Viewed 28 times in the last 48 hours
                                          Excellent! 4.7/5
                                          (21 reviews)
                                          avg/night
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 6
                                          Apartment #4108939
                                          21
                                          Viewed 37 times in the last 48 hours
                                            $50
                                            avg/night
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 4
                                            Apartment #351947vb
                                            4
                                            Viewed 7 times in the last 48 hours
                                              Exceptional! 5.0/5
                                              (15 reviews)
                                              avg/night
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 4
                                              Apartment #609643vb
                                              15
                                              Viewed 10 times in the last 48 hours
                                                • 5 BR
                                                • 2 BA
                                                • Sleeps 12
                                                House #3895901
                                                28
                                                Viewed 36 times in the last 48 hours
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 5
                                                  Cottage #750340vb
                                                  9
                                                    Exceptional! 5.0/5
                                                    (11 reviews)
                                                    avg/night
                                                    • 3 BR
                                                    • 1 BA
                                                    • Sleeps 8
                                                    House #4019811
                                                    11
                                                    Viewed 8 times in the last 48 hours
                                                      Excellent! 4.7/5
                                                      (19 reviews)
                                                      avg/night
                                                      • 3 BR
                                                      • 1 BA
                                                      • Sleeps 5
                                                      Apartment #132084
                                                      19
                                                      Viewed 14 times in the last 48 hours
                                                        Wonderful! 4.8/5
                                                        (73 reviews)
                                                        avg/night
                                                        • 2 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        Apartment #384968vb
                                                        73
                                                        Viewed 18 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (17 reviews)
                                                          avg/night
                                                          • 3 BR
                                                          • 1 BA
                                                          • 1 HF BA
                                                          • Sleeps 6
                                                          House #4034861
                                                          17
                                                          Viewed 20 times in the last 48 hours
                                                            Excellent! 4.6/5
                                                            (44 reviews)
                                                            avg/night
                                                            • 1 BR
                                                            • 2 BA
                                                            • Sleeps 4
                                                            Apartment #3836908
                                                            44
                                                            Viewed 17 times in the last 48 hours
                                                              Exceptional! 5.0/5
                                                              (23 reviews)
                                                              avg/night
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 2
                                                              Apartment #561483vb
                                                              23
                                                              Viewed 6 times in the last 48 hours
                                                                Wonderful! 4.9/5
                                                                (50 reviews)
                                                                avg/night
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                Condo #3849683
                                                                50
                                                                Viewed 18 times in the last 48 hours
                                                                  Excellent! 4.5/5
                                                                  (46 reviews)
                                                                  avg/night
                                                                  • Studio
                                                                  • 1 BA
                                                                  • Sleeps 2
                                                                  Apartment #296086
                                                                  46
                                                                  Viewed 20 times in the last 48 hours
                                                                    Wonderful! 4.8/5
                                                                    (19 reviews)
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 1 BA
                                                                    • Sleeps 4
                                                                    Condo #680805vb
                                                                    19
                                                                    Viewed 10 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (36 reviews)
                                                                      avg/night
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 3
                                                                      Condo #111553
                                                                      36
                                                                      Viewed 17 times in the last 48 hours
                                                                        Wonderful! 4.9/5
                                                                        (10 reviews)
                                                                        $73
                                                                        avg/night
                                                                        • 4 BR
                                                                        • 2 BA
                                                                        • 2 HF BA
                                                                        • Sleeps 9
                                                                        Barn #4054234
                                                                        10
                                                                        Viewed 16 times in the last 48 hours
                                                                          • 4 BR
                                                                          • 1 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 7
                                                                          House #410585vb
                                                                          3
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 4
                                                                            Apartment #784723vb
                                                                            4
                                                                            Viewed 10 times in the last 48 hours
                                                                              Very Good! 4.2/5
                                                                              (10 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 5
                                                                              Apartment #3830991
                                                                              10
                                                                              Viewed 7 times in the last 48 hours
                                                                                Wonderful! 4.8/5
                                                                                (8 reviews)
                                                                                $93
                                                                                avg/night
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 4
                                                                                Cottage #226702
                                                                                8
                                                                                Viewed 19 times in the last 48 hours
                                                                                  Wonderful! 4.9/5
                                                                                  (41 reviews)
                                                                                  avg/night
                                                                                  • 4 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 12
                                                                                  House #592911vb
                                                                                  41
                                                                                  Viewed 27 times in the last 48 hours
                                                                                    Wonderful! 4.8/5
                                                                                    (13 reviews)
                                                                                    avg/night
                                                                                    • 4 BR
                                                                                    • 3 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 8
                                                                                    House #3661538
                                                                                    13
                                                                                    Viewed 8 times in the last 48 hours
                                                                                      Wonderful! 4.9/5
                                                                                      (29 reviews)
                                                                                      avg/night
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 4
                                                                                      Apartment #606119vb
                                                                                      29
                                                                                      Viewed 27 times in the last 48 hours
                                                                                        • 3 BR
                                                                                        • 1 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 4
                                                                                        House #4057736
                                                                                        4
                                                                                          Wonderful! 4.9/5
                                                                                          (60 reviews)
                                                                                          $79
                                                                                          avg/night
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 2
                                                                                          Townhome #630266vb
                                                                                          60
                                                                                          Viewed 43 times in the last 48 hours
                                                                                            Wonderful! 4.8/5
                                                                                            (17 reviews)
                                                                                            avg/night
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 3
                                                                                            Condo #3670822
                                                                                            17
                                                                                            Viewed 5 times in the last 48 hours
                                                                                              Wonderful! 4.8/5
                                                                                              (20 reviews)
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              Apartment #854357vb
                                                                                              20
                                                                                              Viewed 26 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (13 reviews)
                                                                                                avg/night
                                                                                                • 4 BR
                                                                                                • 2 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 8
                                                                                                Townhome #715027vb
                                                                                                13
                                                                                                Viewed 17 times in the last 48 hours
                                                                                                  Wonderful! 4.9/5
                                                                                                  (17 reviews)
                                                                                                  avg/night
                                                                                                  • 5 BR
                                                                                                  • 3 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 11
                                                                                                  House #733403vb
                                                                                                  17
                                                                                                  Viewed 21 times in the last 48 hours
                                                                                                    Very Good! 4.2/5
                                                                                                    (12 reviews)
                                                                                                    avg/night
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 4
                                                                                                    Apartment #3601954
                                                                                                    12
                                                                                                      Wonderful! 4.9/5
                                                                                                      (17 reviews)
                                                                                                      avg/night
                                                                                                      • Studio
                                                                                                      • 1 BA
                                                                                                      • Sleeps 2
                                                                                                      Condo #140088vb
                                                                                                      17
                                                                                                      Viewed 23 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Winchester: Apartments, Houses & More (300+)

                                                                                                       

                                                                                                      Recent Winchester Reviews

                                                                                                      Great place - super close to lots of restaurants and Whole Foods!

                                                                                                      5 of 5
                                                                                                      Before I begin to discuss the property, I have to give a big shot out to Rachel (the owner). My husband and I do a lot of vrbo-ing (we enjoy a kitchen for breakfast) and Rachel is amazing to deal with! A lot of the VRBO owners can be unresponsive or difficult to deal with. Not Rachel- I probably asked her a dozen questions before and during our stay. She was always pleasent and responsive. We brought our dog with us and Rachel was very accommodating. She just asked that we were considerate of others in the area when it came to our dog- which is understandable! The apartment is exactly as described. Very close to lots of restaurants. My husband and I walked everywhere (except to the train station, it was cold!). The apartment is on a street that has a bit of a hill which is nice because it gives you a chance to walk back and digest your food. The kitchen was exactly what we needed and all of the furnishings looked pretty new. The bed was even comfortable- not that 50 year old bed that I've seen in a lot of other places with the springs sticking you in the back. If we make it back up to Boston, I would be happy to stay in this place again!
                                                                                                      • Submitted: Dec 4, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Wonderful stay!

                                                                                                      5 of 5
                                                                                                      My husband and I stayed at Carols condo over a weekend for our first visit to Boston. It was great, well equipped with everything you need and Carol was so friendly and helpful. This is such a better option than a hotel, it really lets you live like a local!
                                                                                                      • Submitted: Nov 28, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Loved it.

                                                                                                      5 of 5
                                                                                                      Great location across the street from Wholefoods and down the street from coffee/pastry shop. Easy walk to a beautiful park. Interior was beautiful. Nice sized kitchen, breakfast and family room. Good sized master and secondary bedrooms. Loved it.
                                                                                                      • Submitted: Nov 22, 2016
                                                                                                      • Stayed: Nov 2016