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
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!

Ossining: Houses, Apartments & More (166)

  • 1 - 50 of 166
    • 3 BR
    • 2 BA
    • 1 HF BA
    • Sleeps 8
      NEW!
      • 6 BR
      • 4 BA
      • 1 HF BA
      • Sleeps 20
      1 Review
        • 6 BR
        • 2 BA
        • 2 HF BA
        • Sleeps 10
        3
          • 2 BR
          • 1 BA
          • 1 HF BA
          • Sleeps 4
          24
            Wonderful! 4.8/5
            (6 reviews)
            avg/night
            • 3 BR
            • 3 BA
            • Sleeps 8
            6
              • 1 BR
              • 1 BA
              • 1 HF BA
              • Sleeps 4
              2 Reviews
                • 1 BR
                • 1 BA
                • Sleeps 2
                1 Review
                  NEW!
                  • 4 BR
                  • 3 BA
                  • 2 HF BA
                  • Sleeps 5
                    • 1 BR
                    • 1 BA
                    • Sleeps 4
                      • 1 BR
                      • 1 BA
                      • Sleeps 2
                        • 1 BR
                        • 1 BA
                        • Sleeps 3
                          NEW!
                          • 4 BR
                          • 3 BA
                          • Sleeps 6
                            • 4 BR
                            • 2 BA
                            • Sleeps 10
                            19
                              NEW!
                              • 1 BR
                              • 1 BA
                              • Sleeps 3
                              1 Review
                                • 6 BR
                                • 5 BA
                                • Sleeps 24
                                26
                                  • 4 BR
                                  • 3 BA
                                  • Sleeps 10
                                  5
                                    NEW!
                                    • 4 BR
                                    • 2 BA
                                    • 1 HF BA
                                    • Sleeps 6
                                    1 Review
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 2
                                        • 5 BR
                                        • 4 BA
                                        • Sleeps 6
                                        1 Review
                                          • 4 BR
                                          • 3 BA
                                          • 1 HF BA
                                          • Sleeps 12
                                          2 Reviews
                                            • 2 BR
                                            • 2 BA
                                            • 1 HF BA
                                            • Sleeps 6
                                            1 Review
                                              • 3 BR
                                              • 3 BA
                                              • 1 HF BA
                                              • Sleeps 7
                                              4
                                                • 4 BR
                                                • 3 BA
                                                • 1 HF BA
                                                • Sleeps 10
                                                  • 3 BR
                                                  • 2 BA
                                                  • 1 HF BA
                                                  • Sleeps 8
                                                    Exceptional! 5.0/5
                                                    (15 reviews)
                                                    avg/night
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    15
                                                      NEW!
                                                      • 5 BR
                                                      • 5 BA
                                                      • Sleeps 10
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        30
                                                          • 5 BR
                                                          • 6 BA
                                                          • Sleeps 12
                                                            • 5 BR
                                                            • 3 BA
                                                            • 1 HF BA
                                                            • Sleeps 13
                                                            7
                                                              • 4 BR
                                                              • 4 BA
                                                              • Sleeps 8
                                                              14
                                                                • 4 BR
                                                                • 4 BA
                                                                • 1 HF BA
                                                                • Sleeps 12
                                                                1 Review
                                                                  • 3 BR
                                                                  • 1 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 6
                                                                    • 3 BR
                                                                    • 3 BA
                                                                    • Sleeps 8
                                                                    2 Reviews
                                                                      • 4 BR
                                                                      • 4 BA
                                                                      • Sleeps 8
                                                                      3
                                                                        Wonderful! 4.9/5
                                                                        (12 reviews)
                                                                        avg/night
                                                                        • 4 BR
                                                                        • 2 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 8
                                                                        12
                                                                          NEW!
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 3
                                                                          2 Reviews
                                                                            NEW!
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 6
                                                                              Excellent! 4.7/5
                                                                              (31 reviews)
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 12
                                                                              31
                                                                                NEW!
                                                                                • 5 BR
                                                                                • 7 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 12
                                                                                  • 3 BR
                                                                                  • 1 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 5
                                                                                  6
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 4
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 2
                                                                                        NEW!
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 4
                                                                                          • 5 BR
                                                                                          • 4 BA
                                                                                          • Sleeps 10
                                                                                            NEW!
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 4
                                                                                              • 3 BR
                                                                                              • 25 BA
                                                                                              • Sleeps 6
                                                                                                NEW!
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 2
                                                                                                  NEW!
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 2
                                                                                                    NEW!
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 2
                                                                                                      NEW!
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 2
                                                                                                      • 1 - 50 of 166
                                                                                                       

                                                                                                      Recent Ossining Reviews

                                                                                                      A Beautiful home with one of a kind views and actual access to shore of the Hudson!

                                                                                                      5 of 5
                                                                                                      While the neighborhood seems a bit rundown- the house is a wonderland of views besides a great kitchen and countless amenities. The house is immaculate and well designed for maximum relaxation and enjoyment.
                                                                                                      • Submitted: Sep 19, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      A great location, with the best hospitality!

                                                                                                      5 of 5
                                                                                                      If your looking for a place to settle in and relax......this is it! The location was perfect for everything we wanted to do. The space offered everything we needed and was exceptionally clean. Though we only saw them upon arrival, Yvonne and Josh were great hosts. Planning to make this stop again! Michael & Susan
                                                                                                      • Submitted: Sep 7, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      Perfect!

                                                                                                      5 of 5
                                                                                                      Best rental we ever had in the NY area. Stayed for 16 days for our son's move to college in Westchester. An immaculately clean, well furnished and comfortable home with everything you need for a short or an extended stay plus a private patio, lounge chairs/table and gas grill - great for having lunch or dinner with friends and family. Well equipped modern kitchen. Perfect cable TV options in every room and speedy WiFi. The shops and restaurants and train station of Port Chester are just minutes away and the location allows an easy commute to NYC, the beaches and main colleges in the area. The unit has free parking right by the house and it is a very quiet, friendly and safe neighborhood. Henri was very helpful and all of the instructions were clear. Definately our choice for the next trip to NY, travelling from Europe.
                                                                                                      • Submitted: Sep 7, 2016
                                                                                                      • Stayed: Aug 2016