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Chester: Houses, Cottages & More (300+)

  • 1 - 50 of 300+
Additional fees apply. Taxes may be added.
    • 3 BR
    • 2 BA
    • 1 HF BA
    • Sleeps 7
    House #3882283
    4
    Viewed 10 times in the last 48 hours
      Wonderful! 4.9/5
      (33 reviews)
      avg/night
      • 2 BR
      • 1 BA
      • 1 HF BA
      • Sleeps 6
      Apartment #563575vb
      33
      Viewed 19 times in the last 48 hours
        Wonderful! 4.8/5
        (33 reviews)
        avg/night
        • 2 BR
        • 1 BA
        • 1 HF BA
        • Sleeps 6
        Bungalow #3767963
        33
        Viewed 19 times in the last 48 hours
          Exceptional! 5.0/5
          (8 reviews)
          avg/night
          • 2 BR
          • 2 BA
          • 1 HF BA
          • Sleeps 6
          Cottage #794843vb
          8
          Viewed 22 times in the last 48 hours
            Exceptional! 5.0/5
            (40 reviews)
            avg/night
            • 4 BR
            • 2 BA
            • 1 HF BA
            • Sleeps 8
            House #392161
            40
            Viewed 12 times in the last 48 hours
              Exceptional! 5.0/5
              (32 reviews)
              avg/night
              • 3 BR
              • 2 BA
              • Sleeps 8
              House #559448vb
              32
              Viewed 27 times in the last 48 hours
                Wonderful! 4.9/5
                (16 reviews)
                avg/night
                • 3 BR
                • 2 BA
                • Sleeps 9
                House #622236vb
                16
                Viewed 27 times in the last 48 hours
                  avg/night
                  • 2 BR
                  • 2 BA
                  • Sleeps 4
                  House #860859vb
                  Viewed 7 times in the last 48 hours
                    Exceptional! 5.0/5
                    (5 reviews)
                    avg/night
                    • 4 BR
                    • 1 BA
                    • 1 HF BA
                    • Sleeps 8
                    Cottage #467665vb
                    5
                      Wonderful! 4.9/5
                      (29 reviews)
                      avg/night
                      • 4 BR
                      • 3 BA
                      • Sleeps 16
                      House #481085vb
                      29
                      Viewed 66 times in the last 48 hours
                        Exceptional! 5.0/5
                        (21 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Sleeps 8
                        House #828761vb
                        21
                        Viewed 50 times in the last 48 hours
                          Exceptional! 5.0/5
                          (9 reviews)
                          avg/night
                          • 4 BR
                          • 2 BA
                          • 1 HF BA
                          • Sleeps 10
                          House #360437
                          9
                          Viewed 29 times in the last 48 hours
                            • 5 BR
                            • 3 BA
                            • 1 HF BA
                            • Sleeps 10
                            House #3976028
                            13
                            Viewed 16 times in the last 48 hours
                              Exceptional! 5.0/5
                              (10 reviews)
                              avg/night
                              • 4 BR
                              • 3 BA
                              • Sleeps 8
                              House #764020vb
                              10
                              Viewed 11 times in the last 48 hours
                                Exceptional! 5.0/5
                                (59 reviews)
                                avg/night
                                • 2 BR
                                • 1 BA
                                • Sleeps 4
                                Apartment #246865
                                59
                                Viewed 12 times in the last 48 hours
                                  Excellent! 4.7/5
                                  (19 reviews)
                                  avg/night
                                  • 1 BR
                                  • 2 BA
                                  • Sleeps 6
                                  Villa #905772
                                  19
                                  Viewed 7 times in the last 48 hours
                                    Exceptional! 5.0/5
                                    (15 reviews)
                                    avg/night
                                    • 2 BR
                                    • 2 BA
                                    • Sleeps 5
                                    Cottage #3903339
                                    15
                                    Viewed 8 times in the last 48 hours
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 6
                                      Cottage #740769vb
                                      4
                                      Viewed 6 times in the last 48 hours
                                        avg/night
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 6
                                        House #4352908
                                        1 Review
                                        Viewed 12 times in the last 48 hours
                                          Exceptional! 5.0/5
                                          (21 reviews)
                                          avg/night
                                          • 4 BR
                                          • 3 BA
                                          • 2 HF BA
                                          • Sleeps 10
                                          Estate #973597
                                          21
                                          Viewed 16 times in the last 48 hours
                                            avg/night
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 5
                                            Cottage #576766vb
                                            4
                                            Viewed 7 times in the last 48 hours
                                              avg/night
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 5
                                              House #4023369
                                              2 Reviews
                                              Viewed 7 times in the last 48 hours
                                                Wonderful! 4.9/5
                                                (8 reviews)
                                                avg/night
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 8
                                                House #4095004
                                                8
                                                Viewed 14 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (14 reviews)
                                                  avg/night
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 5
                                                  House #3554393
                                                  14
                                                  Viewed 32 times in the last 48 hours
                                                    Exceptional! 5.0/5
                                                    (30 reviews)
                                                    avg/night
                                                    • 4 BR
                                                    • 3 BA
                                                    • Sleeps 10
                                                    House #648890vb
                                                    30
                                                    Viewed 35 times in the last 48 hours
                                                      avg/night
                                                      • 4 BR
                                                      • 2 BA
                                                      • Sleeps 8
                                                      House #845751vb
                                                      Viewed 8 times in the last 48 hours
                                                        avg/night
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 2
                                                        Studio #964660vb
                                                        Viewed 19 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (7 reviews)
                                                          avg/night
                                                          • 5 BR
                                                          • 1 BA
                                                          • 1 HF BA
                                                          • Sleeps 8
                                                          Cottage #647079vb
                                                          7
                                                          Viewed 7 times in the last 48 hours
                                                            Exceptional! 5.0/5
                                                            (12 reviews)
                                                            avg/night
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            Cottage #687187vb
                                                            12
                                                            Viewed 14 times in the last 48 hours
                                                              Wonderful! 4.8/5
                                                              (18 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              Apartment #746442vb
                                                              18
                                                              Viewed 15 times in the last 48 hours
                                                                Exceptional! 5.0/5
                                                                (9 reviews)
                                                                avg/night
                                                                • 4 BR
                                                                • 3 BA
                                                                • Sleeps 9
                                                                House #788541vb
                                                                9
                                                                Viewed 14 times in the last 48 hours
                                                                  • 1 BR
                                                                  • 2 BA
                                                                  • Sleeps 2
                                                                  Condo #4276533
                                                                  2 Reviews
                                                                    Exceptional! 5.0/5
                                                                    (5 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 1 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 8
                                                                    House #360132
                                                                    5
                                                                    Viewed 24 times in the last 48 hours
                                                                      avg/night
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      Apartment #739465vb
                                                                      2 Reviews
                                                                      Viewed 11 times in the last 48 hours
                                                                        Wonderful! 4.9/5
                                                                        (10 reviews)
                                                                        avg/night
                                                                        • 5 BR
                                                                        • 3 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 12
                                                                        House #773702vb
                                                                        10
                                                                        Viewed 47 times in the last 48 hours
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 4
                                                                          House #4293415
                                                                          Viewed 13 times in the last 48 hours
                                                                            Excellent! 4.3/5
                                                                            (10 reviews)
                                                                            avg/night
                                                                            • 3 BR
                                                                            • 1 BA
                                                                            • Sleeps 8
                                                                            House #3993156
                                                                            10
                                                                            Viewed 20 times in the last 48 hours
                                                                              • 4 BR
                                                                              • 3 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 11
                                                                              House #914393vb
                                                                              1 Review
                                                                              Viewed 21 times in the last 48 hours
                                                                                Exceptional! 5.0/5
                                                                                (9 reviews)
                                                                                avg/night
                                                                                • 4 BR
                                                                                • 2 BA
                                                                                • Sleeps 10
                                                                                House #747446vb
                                                                                9
                                                                                Viewed 10 times in the last 48 hours
                                                                                  Exceptional! 5.0/5
                                                                                  (5 reviews)
                                                                                  avg/night
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 3
                                                                                  Cottage #835310vb
                                                                                  5
                                                                                  Viewed 8 times in the last 48 hours
                                                                                    Excellent! 4.4/5
                                                                                    (7 reviews)
                                                                                    avg/night
                                                                                    • 4 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 10
                                                                                    Apartment #4178269
                                                                                    7
                                                                                    Viewed 24 times in the last 48 hours
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 10
                                                                                      House #4173935
                                                                                      1 Review
                                                                                      Viewed 13 times in the last 48 hours
                                                                                        avg/night
                                                                                        • 6 BR
                                                                                        • 3 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 10
                                                                                        House #14706vb
                                                                                        1 Review
                                                                                        Viewed 24 times in the last 48 hours
                                                                                          Excellent! 4.7/5
                                                                                          (14 reviews)
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          Condo #607936vb
                                                                                          14
                                                                                          Viewed 14 times in the last 48 hours
                                                                                            Exceptional! 5.0/5
                                                                                            (28 reviews)
                                                                                            avg/night
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 2
                                                                                            Apartment #616070vb
                                                                                            28
                                                                                            Viewed 26 times in the last 48 hours
                                                                                              Wonderful! 4.9/5
                                                                                              (19 reviews)
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 4
                                                                                              Cottage #4068996
                                                                                              19
                                                                                              Viewed 13 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (11 reviews)
                                                                                                avg/night
                                                                                                • 5 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 14
                                                                                                Farmhouse #810873vb
                                                                                                11
                                                                                                Viewed 26 times in the last 48 hours
                                                                                                  Exceptional! 5.0/5
                                                                                                  (21 reviews)
                                                                                                  avg/night
                                                                                                  • 3 BR
                                                                                                  • 1 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 8
                                                                                                  Cottage #473596vb
                                                                                                  21
                                                                                                  Viewed 10 times in the last 48 hours
                                                                                                    Excellent! 4.7/5
                                                                                                    (11 reviews)
                                                                                                    avg/night
                                                                                                    • 4 BR
                                                                                                    • 3 BA
                                                                                                    • 1 HF BA
                                                                                                    • Sleeps 8
                                                                                                    House #227790
                                                                                                    11
                                                                                                      Exceptional! 5.0/5
                                                                                                      (6 reviews)
                                                                                                      avg/night
                                                                                                      • 4 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 10
                                                                                                      House #340957
                                                                                                      6
                                                                                                      Viewed 12 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Chester Reviews

                                                                                                      Excellent hosts! Delightful cottage! Excellent location from Quinnipiac University and Yale!

                                                                                                      5 of 5
                                                                                                      Upon arrival Owner gave us full tour, explained house rules, answered our questions and was extremely welcoming! The walking paths around the river banks are great and the restaurant, less than 2 blocks away, was excellent for our breakfast taste buds. The handmade soaps are fabulous! Our son, 12 years old, and parents loved this place. The beds were super comfy too! The home has everything you've left back home while you're on vacation. We are hoping to visit this gem very soon!
                                                                                                      • Submitted: Nov 28, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Spectacular sunrises, breath taking sunsets!

                                                                                                      5 of 5
                                                                                                      You couldn't ask for more from a beach house. Everything is new and clean. There are water views from practically every room. I even managed to catch a few fish from the beach!
                                                                                                      • Submitted: Nov 20, 2016
                                                                                                      • Stayed: Oct 2016

                                                                                                      Amazing vacation

                                                                                                      5 of 5
                                                                                                      The Bungalow was SOOOOO comfortable. The bed, the soaking tub, kitchen facilities, living room and tv. Location to attractions! We had a great time!!
                                                                                                      • Submitted: Nov 14, 2016
                                                                                                      • Stayed: Nov 2016