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    • 1 BR
    • 1 BA
    • 1 HF BA
    • Sleeps 4
    Cottage #580849
    2
      • 4 BR
      • 3 BA
      • Sleeps 6
      Townhome #4472237ha
        • 4 BR
        • 2 BA
        • Sleeps 7
        House #1079219
        Viewed 9 times in the last 48 hours
          Wonderful! 4.8/5
          (27 reviews)
          avg/night
          • 2 BR
          • 1 BA
          • Sleeps 5
          Apartment #941115ha
          27
          Viewed 54 times in the last 48 hours
            View details for price
            • 2 BR
            • 2 BA
            • Sleeps 4
            Bungalow #3551858ha
            2
            Viewed 7 times in the last 48 hours
              Very Good! 4.2/5
              (6 reviews)
              avg/night
              • 1 BR
              • 1 BA
              • Sleeps 4
              Cottage #991609ha
              6
              Viewed 15 times in the last 48 hours
                • 2 BR
                • 2 BA
                • 1 HF BA
                • Sleeps 6
                House #588047
                4
                Viewed 26 times in the last 48 hours
                  Exceptional! 5/5
                  (6 reviews)
                  $83
                  avg/night
                  • 1 BR
                  • 1 BA
                  • Sleeps 3
                  House #892301
                  6
                  Viewed 26 times in the last 48 hours
                    Excellent! 4.6/5
                    (8 reviews)
                    avg/night
                    • 6 BR
                    • 2 BA
                    • 2 HF BA
                    • Sleeps 10
                    Chateau / Country House #781543
                    8
                    Viewed 12 times in the last 48 hours
                      avg/night
                      • 5 BR
                      • 3 BA
                      • 1 HF BA
                      • Sleeps 8
                      House #981265
                      Viewed 23 times in the last 48 hours
                        Wonderful! 4.9/5
                        (14 reviews)
                        avg/night
                        • 1 BR
                        • 1 BA
                        • Sleeps 4
                        Barn #256842
                        14
                        Viewed 15 times in the last 48 hours
                          Excellent! 4.7/5
                          (11 reviews)
                          avg/night
                          • 2 BR
                          • 1 BA
                          • Sleeps 10
                          House #685435
                          11
                          Viewed 65 times in the last 48 hours
                            Exceptional! 5/5
                            (24 reviews)
                            avg/night
                            • 1 BR
                            • 1 BA
                            • Sleeps 4
                            Cottage #4128981ha
                            24
                            Viewed 60 times in the last 48 hours
                              • 1 BR
                              • 1 BA
                              • Sleeps 2
                              House #4232264ha
                                Excellent! 4.6/5
                                (33 reviews)
                                avg/night
                                • 2 BR
                                • 1 BA
                                • 1 HF BA
                                • Sleeps 4
                                House #3007353ha
                                33
                                Viewed 27 times in the last 48 hours
                                  Excellent! 4.4/5
                                  (5 reviews)
                                  avg/night
                                  • 4 BR
                                  • 2 BA
                                  • 1 HF BA
                                  • Sleeps 8
                                  House #4276853ha
                                  5
                                  Viewed 23 times in the last 48 hours
                                    Exceptional! 5/5
                                    (28 reviews)
                                    avg/night
                                    • 6 BR
                                    • 5 BA
                                    • Sleeps 24
                                    House #3818146ha
                                    28
                                    Viewed 263 times in the last 48 hours
                                      Exceptional! 5/5
                                      (20 reviews)
                                      avg/night
                                      • 4 BR
                                      • 4 BA
                                      • Sleeps 8
                                      House #3941713ha
                                      20
                                      Viewed 36 times in the last 48 hours
                                        Wonderful! 4.8/5
                                        (12 reviews)
                                        avg/night
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 8
                                        House #356609
                                        12
                                        Viewed 12 times in the last 48 hours
                                          • 3 BR
                                          • 3 BA
                                          • Sleeps 5
                                          House #1003348
                                          1
                                          Viewed 9 times in the last 48 hours
                                            avg/night
                                            • 1 BR
                                            • 1 BA
                                            • Sleeps 2
                                            Apartment #1078189
                                            Viewed 6 times in the last 48 hours
                                              • 3 BR
                                              • 2 BA
                                              • 1 HF BA
                                              • Sleeps 6
                                              Townhome #4327021ha
                                              2
                                              Viewed 8 times in the last 48 hours
                                                Excellent! 4.6/5
                                                (19 reviews)
                                                avg/night
                                                • 3 BR
                                                • 1 BA
                                                • 1 HF BA
                                                • Sleeps 4
                                                House #995194ha
                                                19
                                                Viewed 74 times in the last 48 hours
                                                  $90
                                                  avg/night
                                                  • 2 BR
                                                  • 1 BA
                                                  • Sleeps 4
                                                  House #864809
                                                  4
                                                  Viewed 52 times in the last 48 hours
                                                    Exceptional! 5/5
                                                    (5 reviews)
                                                    avg/night
                                                    • 4 BR
                                                    • 2 BA
                                                    • 1 HF BA
                                                    • Sleeps 6
                                                    House #903612
                                                    5
                                                    Viewed 16 times in the last 48 hours
                                                      • 4 BR
                                                      • 3 BA
                                                      • Sleeps 10
                                                      House #995687
                                                      1
                                                      Viewed 25 times in the last 48 hours
                                                        • 6 BR
                                                        • 5 BA
                                                        • 1 HF BA
                                                        • Sleeps 10
                                                        House #901536
                                                        1
                                                        Viewed 13 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (43 reviews)
                                                          avg/night
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 4
                                                          Cottage #3560704ha
                                                          43
                                                          Viewed 57 times in the last 48 hours
                                                            $93
                                                            avg/night
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            Apartment #822726
                                                            2
                                                            Viewed 9 times in the last 48 hours
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 4
                                                              Townhome #935064
                                                              Viewed 29 times in the last 48 hours
                                                                avg/night
                                                                • 1 BR
                                                                • 2 BA
                                                                • Sleeps 3
                                                                House #916556
                                                                1
                                                                Viewed 10 times in the last 48 hours
                                                                  Wonderful! 4.9/5
                                                                  (11 reviews)
                                                                  avg/night
                                                                  • 3 BR
                                                                  • 3 BA
                                                                  • Sleeps 8
                                                                  Villa #916700ha
                                                                  11
                                                                  Viewed 23 times in the last 48 hours
                                                                    Exceptional! 5/5
                                                                    (10 reviews)
                                                                    avg/night
                                                                    • 5 BR
                                                                    • 3 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 13
                                                                    House #225301ha
                                                                    10
                                                                    Viewed 16 times in the last 48 hours
                                                                      • 6 BR
                                                                      • 4 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 11
                                                                      House #4203178ha
                                                                      Viewed 25 times in the last 48 hours
                                                                        avg/night
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • Sleeps 4
                                                                        House #874216
                                                                        Viewed 33 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (33 reviews)
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 4
                                                                          House #377661ha
                                                                          33
                                                                          Viewed 24 times in the last 48 hours
                                                                            Exceptional! 5/5
                                                                            (7 reviews)
                                                                            avg/night
                                                                            • 3 BR
                                                                            • 3 BA
                                                                            • Sleeps 8
                                                                            House #853457
                                                                            7
                                                                            Viewed 26 times in the last 48 hours
                                                                              avg/night
                                                                              • 4 BR
                                                                              • 3 BA
                                                                              • 2 HF BA
                                                                              • Sleeps 7
                                                                              House #912505
                                                                              1
                                                                              Viewed 43 times in the last 48 hours
                                                                                Excellent! 4.4/5
                                                                                (14 reviews)
                                                                                avg/night
                                                                                • 4 BR
                                                                                • 3 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 8
                                                                                House #124005ha
                                                                                14
                                                                                Viewed 44 times in the last 48 hours
                                                                                  Wonderful! 4.8/5
                                                                                  (10 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 1 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 5
                                                                                  Townhome #4104783ha
                                                                                  10
                                                                                  Viewed 6 times in the last 48 hours
                                                                                    • 5 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 10
                                                                                    House #458986
                                                                                    1
                                                                                    Viewed 38 times in the last 48 hours
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 8
                                                                                      House #820899
                                                                                      1
                                                                                      Viewed 14 times in the last 48 hours
                                                                                        Wonderful! 4.8/5
                                                                                        (25 reviews)
                                                                                        avg/night
                                                                                        • 4 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 10
                                                                                        Farmhouse #3783517ha
                                                                                        25
                                                                                        Viewed 22 times in the last 48 hours
                                                                                          • 4 BR
                                                                                          • 3 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 12
                                                                                          Estate #4194596ha
                                                                                          2
                                                                                          Viewed 23 times in the last 48 hours
                                                                                            avg/night
                                                                                            • 4 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 6
                                                                                            House #4445895ha
                                                                                            Viewed 9 times in the last 48 hours
                                                                                              Exceptional! 5/5
                                                                                              (4 reviews)
                                                                                              avg/night
                                                                                              • 4 BR
                                                                                              • 2 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 7
                                                                                              House #587787
                                                                                              4
                                                                                              Viewed 26 times in the last 48 hours
                                                                                                Wonderful! 4.8/5
                                                                                                (4 reviews)
                                                                                                avg/night
                                                                                                • 8 BR
                                                                                                • 5 BA
                                                                                                • 2 HF BA
                                                                                                • Sleeps 30
                                                                                                Estate #668283
                                                                                                4
                                                                                                Viewed 38 times in the last 48 hours
                                                                                                  avg/night
                                                                                                  • 5 BR
                                                                                                  • 3 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 11
                                                                                                  House #4439121ha
                                                                                                  3
                                                                                                  Viewed 16 times in the last 48 hours
                                                                                                    • 5 BR
                                                                                                    • 3 BA
                                                                                                    • 1 HF BA
                                                                                                    • Sleeps 10
                                                                                                    House #977525
                                                                                                    3
                                                                                                    Viewed 16 times in the last 48 hours
                                                                                                      avg/night
                                                                                                      • 2 BR
                                                                                                      • 1 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 4
                                                                                                      House #4199443ha
                                                                                                      3
                                                                                                      Viewed 13 times in the last 48 hours
                                                                                                      • 1 - 50 of 170
                                                                                                       

                                                                                                      Recent Chappaqua Reviews

                                                                                                      Lovely Home in SW CT

                                                                                                      5 of 5
                                                                                                      Absolutely lovely home! Very welcoming and comfy for our party of six adults. Lots of room for everyone to have their own space and privacy plus a large dining/family room for spending time together. Deirdre was a wonderful hostess who graciously accommodated our three small dogs as well. The property was beautiful with its large, shady backyard. We loved walking out back to check out the birds and other wildlife...lots of chipmunks, a very shy groundhog, and deer that liked to graze around the pond. Conveniently located with easy access to dining, shopping and the Stamford train station for day trips to NYC. The perfect home away from home!
                                                                                                      • Submitted: Jun 27, 2017
                                                                                                      • Stayed: Jun 2017

                                                                                                      Stunning house, great times. We want to go back!

                                                                                                      5 of 5
                                                                                                      Where to start. This house is breathtaking. Gorgeous, modern, clean, spacious, restful and fun. The beds and bathrooms are luxe to the max, the kitchen and living rooms wide open and accommodating, the indoor pool area gorgeous. And yet it's the price-per-person of a hotel room if you fill it with a large group. We were there for West Point graduation 2017, and it was 12 minutes away. And those views ... You're on a hilltop and the house has sweeping decks everywhere looking over the Hudson and the towns adjacent to West Point. One poignant touch for us was that on graduation night, we were on the deck and could see Michie Stadium still lit up from our son's commencement that morning. Unforgettable. Shea is wonderful to work with, very responsive and very very considerate. This house and Shea's hospitality helped make grad week epic for us. Cannot recommend highly enough!!!
                                                                                                      • Submitted: Jun 12, 2017
                                                                                                      • Stayed: May 2017