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!

Chesterfield: Houses, Cottages & More (300+)

  • 1 - 50 of 300+
Additional fees apply. Taxes may be added.
    Exceptional! 5.0/5
    (23 reviews)
    avg/night
    • 1 BR
    • 1 BA
    • Sleeps 4
    Cottage #4018430
    23
    Viewed 26 times in the last 48 hours
      Wonderful! 4.8/5
      (13 reviews)
      avg/night
      • 2 BR
      • 1 BA
      • Sleeps 4
      Cabin #450731vb
      13
      Viewed 13 times in the last 48 hours
        avg/night
        • 4 BR
        • 2 BA
        • 1 HF BA
        • Sleeps 8
        House #606789vb
        3
        Viewed 5 times in the last 48 hours
          Exceptional! 5.0/5
          (8 reviews)
          $83
          avg/night
          • 1 BR
          • 1 BA
          • Sleeps 4
          Apartment #4069856
          8
          Viewed 6 times in the last 48 hours
            Exceptional! 5.0/5
            (12 reviews)
            avg/night
            • 6 BR
            • 5 BA
            • Sleeps 20
            Estate #4258796
            12
            Viewed 86 times in the last 48 hours
              Wonderful! 4.9/5
              (9 reviews)
              avg/night
              • 3 BR
              • 2 BA
              • Sleeps 7
              House #330190
              9
                • 2 BR
                • 3 BA
                • Sleeps 5
                House #741610vb
                2 Reviews
                  $64
                  avg/night
                  • 1 BR
                  • 1 BA
                  • Sleeps 4
                  Apartment #4119879
                  2 Reviews
                  Viewed 7 times in the last 48 hours
                    Exceptional! 5.0/5
                    (17 reviews)
                    avg/night
                    • 6 BR
                    • 4 BA
                    • 1 HF BA
                    • Sleeps 12
                    Estate #629154vb
                    17
                    Viewed 6 times in the last 48 hours
                      Wonderful! 4.9/5
                      (10 reviews)
                      avg/night
                      • 4 BR
                      • 2 BA
                      • 1 HF BA
                      • Sleeps 8
                      Farmhouse #627684vb
                      10
                      Viewed 8 times in the last 48 hours
                        Excellent! 4.5/5
                        (14 reviews)
                        avg/night
                        • 2 BR
                        • 1 BA
                        • Sleeps 6
                        Apartment #293804
                        14
                        Viewed 10 times in the last 48 hours
                          Wonderful! 4.9/5
                          (18 reviews)
                          avg/night
                          • 2 BR
                          • 1 BA
                          • Sleeps 5
                          Cottage #707780vb
                          18
                          Viewed 26 times in the last 48 hours
                            Excellent! 4.7/5
                            (6 reviews)
                            avg/night
                            • 1 BR
                            • 1 BA
                            • Sleeps 4
                            Apartment #630224vb
                            6
                            Viewed 9 times in the last 48 hours
                              Excellent! 4.6/5
                              (48 reviews)
                              avg/night
                              • 2 BR
                              • 1 BA
                              • Sleeps 4
                              Cabin #182224
                              48
                              Viewed 21 times in the last 48 hours
                                Exceptional! 5.0/5
                                (21 reviews)
                                avg/night
                                • 5 BR
                                • 5 BA
                                • Sleeps 12
                                House #729783vb
                                21
                                  Wonderful! 4.8/5
                                  (37 reviews)
                                  avg/night
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 6
                                  Cottage #293009
                                  37
                                  Viewed 33 times in the last 48 hours
                                    Exceptional! 5.0/5
                                    (15 reviews)
                                    avg/night
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 5
                                    Apartment #334295
                                    15
                                    Viewed 14 times in the last 48 hours
                                      Wonderful! 4.8/5
                                      (22 reviews)
                                      avg/night
                                      • 7 BR
                                      • 3 BA
                                      • Sleeps 10
                                      Farmhouse #444851vb
                                      22
                                      Viewed 30 times in the last 48 hours
                                        Exceptional! 5.0/5
                                        (9 reviews)
                                        avg/night
                                        • 6 BR
                                        • 3 BA
                                        • Sleeps 10
                                        House #4064007
                                        9
                                        Viewed 15 times in the last 48 hours
                                          Excellent! 4.7/5
                                          (9 reviews)
                                          avg/night
                                          • 3 BR
                                          • 1 BA
                                          • 1 HF BA
                                          • Sleeps 6
                                          Chateau / Country House #4149878
                                          9
                                          Viewed 12 times in the last 48 hours
                                            • 2 BR
                                            • 2 BA
                                            • Sleeps 6
                                            Cottage #3790476
                                            9
                                              Wonderful! 4.8/5
                                              (22 reviews)
                                              avg/night
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 5
                                              Cabin #189705vb
                                              22
                                              Viewed 8 times in the last 48 hours
                                                Wonderful! 4.9/5
                                                (27 reviews)
                                                avg/night
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 12
                                                House #420727vb
                                                27
                                                Viewed 9 times in the last 48 hours
                                                  Very Good! 4.0/5
                                                  (8 reviews)
                                                  avg/night
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 7
                                                  House #344576vb
                                                  8
                                                  Viewed 14 times in the last 48 hours
                                                    • 3 BR
                                                    • 1 BA
                                                    • 1 HF BA
                                                    • Sleeps 6
                                                    House #602972vb
                                                    3
                                                    Viewed 8 times in the last 48 hours
                                                      avg/night
                                                      • 4 BR
                                                      • 2 BA
                                                      • Sleeps 8
                                                      House #711169vb
                                                      3
                                                      Viewed 7 times in the last 48 hours
                                                        Exceptional! 5.0/5
                                                        (20 reviews)
                                                        avg/night
                                                        • 3 BR
                                                        • 3 BA
                                                        • Sleeps 8
                                                        House #224680
                                                        20
                                                        Viewed 18 times in the last 48 hours
                                                          Exceptional! 5.0/5
                                                          (14 reviews)
                                                          avg/night
                                                          • 5 BR
                                                          • 2 BA
                                                          • 1 HF BA
                                                          • Sleeps 10
                                                          Barn #616214vb
                                                          14
                                                          Viewed 23 times in the last 48 hours
                                                            Exceptional! 5.0/5
                                                            (8 reviews)
                                                            avg/night
                                                            • 4 BR
                                                            • 2 BA
                                                            • Sleeps 7
                                                            House #509787vb
                                                            8
                                                            Viewed 8 times in the last 48 hours
                                                              Exceptional! 5.0/5
                                                              (15 reviews)
                                                              avg/night
                                                              • 4 BR
                                                              • 3 BA
                                                              • 1 HF BA
                                                              • Sleeps 12
                                                              House #583082vb
                                                              15
                                                              Viewed 31 times in the last 48 hours
                                                                Excellent! 4.7/5
                                                                (11 reviews)
                                                                avg/night
                                                                • 3 BR
                                                                • 2 BA
                                                                • 1 HF BA
                                                                • Sleeps 8
                                                                House #607741vb
                                                                11
                                                                Viewed 6 times in the last 48 hours
                                                                  Wonderful! 4.8/5
                                                                  (13 reviews)
                                                                  avg/night
                                                                  • 5 BR
                                                                  • 2 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 12
                                                                  House #561543vb
                                                                  13
                                                                  Viewed 9 times in the last 48 hours
                                                                    • 5 BR
                                                                    • 4 BA
                                                                    • Sleeps 10
                                                                    House #3959837
                                                                    12
                                                                    Viewed 27 times in the last 48 hours
                                                                      Excellent! 4.7/5
                                                                      (38 reviews)
                                                                      avg/night
                                                                      • 4 BR
                                                                      • 1 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 8
                                                                      House #332468
                                                                      38
                                                                      Viewed 23 times in the last 48 hours
                                                                        Exceptional! 5.0/5
                                                                        (6 reviews)
                                                                        avg/night
                                                                        • 2 BR
                                                                        • 1 BA
                                                                        • Sleeps 6
                                                                        Condo #3712818
                                                                        6
                                                                        Viewed 6 times in the last 48 hours
                                                                          Exceptional! 5.0/5
                                                                          (16 reviews)
                                                                          avg/night
                                                                          • 3 BR
                                                                          • 1 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 8
                                                                          House #3811779
                                                                          16
                                                                          Viewed 12 times in the last 48 hours
                                                                            Wonderful! 4.8/5
                                                                            (21 reviews)
                                                                            avg/night
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 10
                                                                            House #503722vb
                                                                            21
                                                                            Viewed 6 times in the last 48 hours
                                                                              Excellent! 4.6/5
                                                                              (20 reviews)
                                                                              $83
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 10
                                                                              House #283894vb
                                                                              20
                                                                              Viewed 11 times in the last 48 hours
                                                                                Wonderful! 4.9/5
                                                                                (15 reviews)
                                                                                avg/night
                                                                                • 6 BR
                                                                                • 6 BA
                                                                                • Sleeps 12
                                                                                Estate #568397vb
                                                                                15
                                                                                Viewed 17 times in the last 48 hours
                                                                                  Excellent! 4.4/5
                                                                                  (11 reviews)
                                                                                  avg/night
                                                                                  • 2 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  House #3860654
                                                                                  11
                                                                                  Viewed 14 times in the last 48 hours
                                                                                    Wonderful! 4.9/5
                                                                                    (14 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 6
                                                                                    House #3720156
                                                                                    14
                                                                                      Exceptional! 5.0/5
                                                                                      (28 reviews)
                                                                                      avg/night
                                                                                      • 4 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 8
                                                                                      House #346304vb
                                                                                      28
                                                                                      Viewed 15 times in the last 48 hours
                                                                                        Exceptional! 5.0/5
                                                                                        (14 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        Apartment #3942533
                                                                                        14
                                                                                          Exceptional! 5.0/5
                                                                                          (20 reviews)
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 6
                                                                                          House #381805vb
                                                                                          20
                                                                                          Viewed 5 times in the last 48 hours
                                                                                            Wonderful! 4.9/5
                                                                                            (47 reviews)
                                                                                            avg/night
                                                                                            • 4 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 10
                                                                                            House #3903608
                                                                                            47
                                                                                            Viewed 19 times in the last 48 hours
                                                                                              avg/night
                                                                                              • 5 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 8
                                                                                              House #4160350
                                                                                              4
                                                                                              Viewed 5 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (10 reviews)
                                                                                                avg/night
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 6
                                                                                                Cottage #361931vb
                                                                                                10
                                                                                                Viewed 12 times in the last 48 hours
                                                                                                  Wonderful! 4.8/5
                                                                                                  (17 reviews)
                                                                                                  avg/night
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 8
                                                                                                  Chateau / Country House #379845vb
                                                                                                  17
                                                                                                  Viewed 8 times in the last 48 hours
                                                                                                    • 5 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 10
                                                                                                    Lodge #487322vb
                                                                                                    4
                                                                                                    Viewed 5 times in the last 48 hours
                                                                                                      Wonderful! 4.9/5
                                                                                                      (17 reviews)
                                                                                                      avg/night
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
                                                                                                      House #3893831
                                                                                                      17
                                                                                                      Viewed 11 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Chesterfield Reviews

                                                                                                      Lovely!

                                                                                                      5 of 5
                                                                                                      What a warm and charming cottage! The location is extremely convenient. Ruth and Gareth were very welcoming. We will stay agian.
                                                                                                      • Submitted: Dec 1, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      It was a wonderful weekend getaway.

                                                                                                      4 of 5
                                                                                                      Djuna has a clean, welcoming home. It was spacious and had the necessary equipment for my weekend trip with 3 other people. I wish the heat was controllable by the us and not the owner. Besides that the communication between Djuna was minimal. Once in contact with her, she was flexible and nice. I'd consider returning back to the property in the summer. Thanks for renting out your space!
                                                                                                      • Submitted: Nov 30, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Thanksgiving

                                                                                                      5 of 5
                                                                                                      What a delight to arrive at the house to find 6 inches of fresh snow! My grandson and I made a snow man while the fire cracked away in the fire pit. We all loved the house and the kitchen is amazing! After we all hiked in the cold and the snow, my entire family enjoyed a quick warm up thanks to the radiant heat tiles in the kitchen. My three little ones also loved the Roman style bathtub. The owner is a great guy and responds quickly to emails, texts, of calls. We can't wait to return. One of our best holidays!
                                                                                                      • Submitted: Nov 27, 2016
                                                                                                      • Stayed: Nov 2016