Cottages in Chestertown and Apartments – Holiday Lettings - Holiday Rentals Chestertown

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117 Holiday homes

(19) Excellent 

    36

    Holiday home in Chestertown

    New York / Chestertown

    3 8 min stay varies

    • 3 bedrooms
    • sleeps 8
    • min stay varies
    • Beach / lakeside relaxation
    • Child friendly

    from £178 / night

    £1,153 - £1,330 / week

    Book View

    Responds fast!
    avg. 1 hour 27 minutes

    from £178 / night

    (17) Excellent 

    Certificate of Excellence

      25

      Chestertown ski apartment to rent.

      New York / Chestertown

      2 6 min stay varies

      • 2 bedrooms
      • sleeps 6
      • min stay varies
      • Beach / lakeside relaxation
      • Nearest beach 0 km
      • Ski

      Certificate of Excellence

      from £133 / night

      £577 - £887 / week

      Book View

      Responds fast!
      avg. 2 hours 3 minutes

      from £133 / night

      (13) Excellent 

        34

        Cottage rental in Chestertown

        New York / Chestertown

        4 10 min stay varies

        • 4 bedrooms
        • sleeps 10
        • min stay varies
        • Beach / lakeside relaxation
        • Nearest beach 26 km
        • Child friendly

        from £355 / night

        £2,482 - £3,280 / week

        Book View

        from £355 / night

        (2) Very Good 

          22

          Chestertown holiday cottage rental

          New York / Chestertown

          2 7 2 nights min

          • 2 bedrooms
          • sleeps 7
          • 2 nights min
          • Beach / lakeside relaxation
          • Nearest beach 0.1 km
          • Child friendly

          from £177 / night

          £1,063 - £1,218 / week

          Book View

          Responds fast!
          avg. 2 hours 45 minutes

          from £177 / night

          (13) Excellent 

            12

            Chestertown holiday log cabin rental

            New York / Chestertown

            2 4 2 nights min

            • 2 bedrooms
            • sleeps 4
            • 2 nights min
            • Nearest beach 5 km
            • Child friendly
            • Private garden

            from £133 / night

            £843 / week

            Book View

            from £133 / night

            (6) Excellent 

              23

              B&b rental in Chestertown

              New York / Chestertown

              2 4 2 nights min

              • 2 bedrooms
              • sleeps 4
              • 2 nights min
              • Beach / lakeside relaxation
              • Child friendly

              from £222 / night

              £1,552 - £2,394 / week

              Book View

              from £222 / night

              Great rentals within 20 miles that match your search

              Distance approx 12.6 miles from Chestertown

              (1) Excellent 

                17

                Schroon Lake holiday home rental

                New York / Schroon Lake

                5 12 7 nights min

                • 5 bedrooms
                • sleeps 12
                • 7 nights min
                • Child friendly
                • Air conditioning
                • Pet friendly

                from £190 / night

                £1,330 - £1,596 / week

                Book View

                from £190 / night

                Distance approx 19.74 miles from Chestertown

                (2) Excellent 

                  8

                  Lake Luzerne holiday home rental

                  New York / Lake Luzerne

                  3 5 6 nights min

                  • 3 bedrooms
                  • sleeps 5
                  • 6 nights min
                  • Child friendly
                  • Ask about pets
                  • Private garden

                  from £169 / night

                  £1,179 / week

                  Book View

                  from £169 / night

                  Distance approx 9.71 miles from Chestertown Show on Map

                    15

                    Holiday home in North Creek

                    New York / North Creek

                    5 12 2 nights min

                    • 5 bedrooms
                    • sleeps 12
                    • 2 nights min
                    • Suitable for children age 5+
                    • Ask about pets

                    from £311 / night

                    £1,773 - £1,897 / week

                    Book View

                    from £311 / night

                    Distance approx 16.09 miles from Chestertown

                      11

                      Holiday home in Severance

                      New York / Severance

                      3 8 2 nights min

                      • 3 bedrooms
                      • sleeps 8
                      • 2 nights min
                      • Beach / lakeside relaxation
                      • Child friendly
                      • Pet friendly

                      from £200 / night

                      £1,131 - £1,778 / week

                      Book View

                      from £200 / night

                      Distance approx 15.6 miles from Chestertown

                        31

                        Holiday tented camp in North River

                        New York / North River

                        1 2 1 night min

                        • 1 bedroom
                        • sleeps 2
                        • 1 night min
                        • Beach / lakeside relaxation
                        • Child friendly

                        from £120 / night

                        £798 / week

                        Book View

                        Responds fast!
                        avg. 2 hours 1 minutes

                        from £120 / night

                        Distance approx 16.52 miles from Chestertown

                          21

                          Holiday home rental

                          New York / Schroon Lake

                          4 8 7 nights min

                          • 4 bedrooms
                          • sleeps 8
                          • 7 nights min
                          • Child friendly
                          • Private garden

                          from £380 / night

                          £2,660 / week

                          Book View

                          Responds fast!
                          avg. 3 hours 35 minutes

                          from £380 / night

                          Distance approx 17.06 miles from Chestertown

                          (2) Excellent 

                            17

                            Lake George holiday home rental

                            New York / Lake George

                            4 11 7 nights min

                            • 4 bedrooms
                            • sleeps 11
                            • 7 nights min
                            • Child friendly
                            • Air conditioning

                            from £343 / night

                            £2,394 / week

                            Book View

                            from £343 / night

                            Distance approx 16.06 miles from Chestertown

                              11

                              Holiday home in Severance

                              New York / Severance

                              3 6 min stay varies

                              • 3 bedrooms
                              • sleeps 6
                              • min stay varies
                              • Beach / lakeside relaxation
                              • Nearest beach 0 km
                              • Child friendly

                              from £213 / night

                              £1,330 - £1,685 / week

                              Book View

                              from £213 / night

                              Distance approx 16.02 miles from Chestertown

                                5

                                Holiday home in Severance

                                New York / Severance

                                4 6 7 nights min

                                • 4 bedrooms
                                • sleeps 6
                                • 7 nights min
                                • Beach / lakeside relaxation
                                • Nearest beach 0 km
                                • Child friendly

                                from £228 / night

                                £1,596 / week

                                Book View

                                from £228 / night

                                Distance approx 8.47 miles from Chestertown

                                  8

                                  Holiday home in Lake George

                                  New York / Lake George

                                  2 6 2 nights min

                                  • 2 bedrooms
                                  • sleeps 6
                                  • 2 nights min
                                  • Child friendly
                                  • Air conditioning
                                  • Ask about pets

                                  from £160 / night

                                  £1,002 / week

                                  Book View

                                  from £160 / night

                                  Distance approx 8.47 miles from Chestertown

                                  (1) Excellent 

                                    6

                                    Lake George holiday home rental

                                    New York / Lake George

                                    2 6 2 nights min

                                    • 2 bedrooms
                                    • sleeps 6
                                    • 2 nights min
                                    • Beach / lakeside relaxation
                                    • Child friendly
                                    • Air conditioning

                                    from £151 / night

                                    £940 / week

                                    Book View

                                    from £151 / night

                                    Distance approx 15.04 miles from Chestertown

                                    (1) Excellent 

                                      17

                                      Tented camp rental in North River

                                      New York / North River

                                      1 4 1 night min

                                      • 1 bedroom
                                      • sleeps 4
                                      • 1 night min
                                      • Child friendly

                                      from £129 / night

                                      £900 / week

                                      Book View

                                      Responds fast!
                                      avg. 2 hours 1 minutes

                                      from £129 / night

                                      Distance approx 8.47 miles from Chestertown

                                      (4) Average 

                                        8

                                        Holiday cottage in Lake George

                                        New York / Lake George

                                        4 8 1 night min

                                        • 4 bedrooms
                                        • sleeps 8
                                        • 1 night min
                                        • Beach / lakeside relaxation
                                        • Child friendly
                                        • Air conditioning

                                        from £164 / night

                                        £1,038 / week

                                        Book View

                                        from £164 / night

                                        Distance approx 16.81 miles from Chestertown

                                        (1) Excellent 

                                          10

                                          Lake George holiday cottage rental

                                          New York / Lake George

                                          2 7 3 nights min

                                          • 2 bedrooms
                                          • sleeps 7
                                          • 3 nights min
                                          • Child friendly
                                          • Pet friendly
                                          • Private garden

                                          from £244 / night

                                          £1,685 / week

                                          Book View

                                          from £244 / night

                                          Distance approx 12.29 miles from Chestertown

                                            10

                                            Holiday chalet in Bakers Mills

                                            New York / Bakers Mills

                                            3 8 1 night min

                                            • 3 bedrooms
                                            • sleeps 8
                                            • 1 night min
                                            • Child friendly

                                            from £222 / night

                                            £1,197 - £1,507 / week

                                            Book View

                                            from £222 / night

                                            Distance approx 9.05 miles from Chestertown

                                            (2) Very Good 

                                              15

                                              Bolton Landing holiday home rental

                                              New York / Bolton Landing

                                              3 8 min stay varies

                                              • 3 bedrooms
                                              • sleeps 8
                                              • min stay varies
                                              • Child friendly
                                              • Air conditioning
                                              • Pet friendly

                                              from £222 / night

                                              £1,552 / week

                                              Book View

                                              from £222 / night

                                              Distance approx 3.33 miles from Chestertown Show on Map

                                              (1) Excellent 

                                                29

                                                Riparius holiday cottage rental

                                                New York / Riparius

                                                3 6 2 nights min

                                                • 3 bedrooms
                                                • sleeps 6
                                                • 2 nights min
                                                • Nearest beach 0.25 km
                                                • Child friendly
                                                • Private garden

                                                from £200 / night

                                                £1,086 / week

                                                Book View

                                                from £200 / night

                                                Distance approx 8.47 miles from Chestertown

                                                  1

                                                  Cottage rental in Lake George

                                                  New York / Lake George

                                                  1 3 1 night min

                                                  • 1 bedroom
                                                  • sleeps 3
                                                  • 1 night min
                                                  • Beach / lakeside relaxation
                                                  • Child friendly
                                                  • Air conditioning

                                                  from £96 / night

                                                  £648 / week

                                                  Book View

                                                  from £96 / night

                                                  Distance approx 16.52 miles from Chestertown

                                                    18

                                                    Holiday home in Schroon Lake

                                                    New York / Schroon Lake

                                                    4 8 7 nights min

                                                    • 4 bedrooms
                                                    • sleeps 8
                                                    • 7 nights min
                                                    • Child friendly
                                                    • Private garden

                                                    from £380 / night

                                                    £2,660 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 3 hours 35 minutes

                                                    from £380 / night

                                                    Distance approx 11.59 miles from Chestertown

                                                      17

                                                      Ski log cabin to rent in Johnsburg

                                                      New York / Johnsburg

                                                      3 16 3 nights min

                                                      • 3 bedrooms
                                                      • sleeps 16
                                                      • 3 nights min
                                                      • Beach / lakeside relaxation
                                                      • Ski
                                                      • Child friendly

                                                      from £532 / night

                                                      £2,660 / week

                                                      Book View

                                                      from £532 / night

                                                      Distance approx 8.47 miles from Chestertown

                                                      (2)  

                                                        6

                                                        Lake George holiday apartment rental

                                                        New York / Lake George

                                                        3 8 2 nights min

                                                        • 3 bedrooms
                                                        • sleeps 8
                                                        • 2 nights min
                                                        • Beach / lakeside relaxation
                                                        • Child friendly
                                                        • Air conditioning

                                                        from £169 / night

                                                        £1,064 / week

                                                        Book View

                                                        from £169 / night

                                                        Distance approx 16.81 miles from Chestertown

                                                        (1) Very Good 

                                                          6

                                                          Holiday cottage rental

                                                          New York / Lake George

                                                          2 6 3 nights min

                                                          • 2 bedrooms
                                                          • sleeps 6
                                                          • 3 nights min
                                                          • Child friendly
                                                          • Pet friendly
                                                          • Private garden

                                                          from £222 / night

                                                          £1,596 / week

                                                          Book View

                                                          from £222 / night

                                                          Distance approx 8.47 miles from Chestertown

                                                          (1) Very Good 

                                                            5

                                                            Holiday home in Diamond Point

                                                            Lake George / Diamond Point

                                                            3 8 2 nights min

                                                            • 3 bedrooms
                                                            • sleeps 8
                                                            • 2 nights min
                                                            • Beach / lakeside relaxation
                                                            • Air conditioning
                                                            • Pet friendly

                                                            from £169 / night

                                                            £1,038 / week

                                                            Book View

                                                            from £169 / night

                                                            Distance approx 8.47 miles from Chestertown

                                                            (1) Very Good 

                                                              5

                                                              Holiday home in Lake George

                                                              New York / Lake George

                                                              6 16 2 nights min

                                                              • 6 bedrooms
                                                              • sleeps 16
                                                              • 2 nights min
                                                              • Beach / lakeside relaxation
                                                              • Child friendly
                                                              • Air conditioning

                                                              from £328 / night

                                                              £1,951 / week

                                                              Book View

                                                              from £328 / night

                                                              Distance approx 8.47 miles from Chestertown

                                                              (2) Very Good 

                                                                6

                                                                Lake George holiday apartment rental

                                                                New York / Lake George

                                                                1 4 2 nights min

                                                                • 1 bedroom
                                                                • sleeps 4
                                                                • 2 nights min
                                                                • Beach / lakeside relaxation
                                                                • Child friendly
                                                                • Air conditioning

                                                                from £147 / night

                                                                £843 / week

                                                                Book View

                                                                from £147 / night

                                                                Distance approx 15.37 miles from Chestertown

                                                                  19

                                                                  Lake George holiday cottage rental

                                                                  New York / Lake George

                                                                  1 4 min stay varies

                                                                  • 1 bedroom
                                                                  • sleeps 4
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Child friendly
                                                                  • Air conditioning

                                                                  from £98 / night

                                                                  £537 - £718 / week

                                                                  Book View

                                                                  from £98 / night

                                                                  Distance approx 11.7 miles from Chestertown

                                                                    13

                                                                    Diamond Point holiday cottage rental

                                                                    Lake George / Diamond Point

                                                                    3 6 7 nights min

                                                                    • 3 bedrooms
                                                                    • sleeps 6
                                                                    • 7 nights min
                                                                    • Nearest beach 0 km
                                                                    • Child friendly
                                                                    • Air conditioning

                                                                    from £406 / night

                                                                    £2,837 / week

                                                                    Book View

                                                                    from £406 / night

                                                                    Distance approx 15.37 miles from Chestertown

                                                                      17

                                                                      Cottage rental in Lake George with shared pool

                                                                      New York / Lake George

                                                                      2 4 min stay varies

                                                                      • 2 bedrooms
                                                                      • sleeps 4
                                                                      • min stay varies
                                                                      • Swimming pool
                                                                      • Child friendly
                                                                      • Air conditioning

                                                                      from £98 / night

                                                                      £568 - £741 / week

                                                                      Book View

                                                                      from £98 / night

                                                                      Distance approx 15.05 miles from Chestertown

                                                                        13

                                                                        Holiday cottage in Cleverdale

                                                                        New York / Cleverdale

                                                                        1 3 30 nights min

                                                                        • 1 bedroom
                                                                        • sleeps 3
                                                                        • 30 nights min

                                                                        from £178 / night

                                                                        £1,241 / week

                                                                        Book View

                                                                        from £178 / night

                                                                        Distance approx 15.37 miles from Chestertown

                                                                          11

                                                                          Holiday cottage with shared pool in Lake George

                                                                          New York / Lake George

                                                                          2 8 min stay varies

                                                                          • 2 bedrooms
                                                                          • sleeps 8
                                                                          • min stay varies
                                                                          • Swimming pool
                                                                          • Child friendly
                                                                          • Air conditioning

                                                                          from £116 / night

                                                                          £625 - £993 / week

                                                                          Book View

                                                                          from £116 / night

                                                                          Distance approx 14.4 miles from Chestertown

                                                                          (2) Excellent 

                                                                            20

                                                                            Diamond Point holiday cottage rental

                                                                            Lake George / Diamond Point

                                                                            2 4 6 nights min

                                                                            • 2 bedrooms
                                                                            • sleeps 4
                                                                            • 6 nights min
                                                                            • Beach / lakeside relaxation
                                                                            • Nearest beach 1 km
                                                                            • Child friendly

                                                                            from £70 / night

                                                                            £491 / week

                                                                            Book View

                                                                            Responds fast!
                                                                            avg. 2 hours 29 minutes

                                                                            from £70 / night

                                                                            Distance approx 15.37 miles from Chestertown

                                                                              12

                                                                              Holiday cottage with shared pool in Lake George

                                                                              New York / Lake George

                                                                              2 4 min stay varies

                                                                              • 2 bedrooms
                                                                              • sleeps 4
                                                                              • min stay varies
                                                                              • Swimming pool
                                                                              • Child friendly
                                                                              • Air conditioning

                                                                              from £120 / night

                                                                              £656 - £829 / week

                                                                              Book View

                                                                              from £120 / night

                                                                              Distance approx 15.37 miles from Chestertown

                                                                                17

                                                                                Lake George holiday cottage rental

                                                                                New York / Lake George

                                                                                2 4 min stay varies

                                                                                • 2 bedrooms
                                                                                • sleeps 4
                                                                                • min stay varies
                                                                                • Swimming pool
                                                                                • Child friendly
                                                                                • Air conditioning

                                                                                from £120 / night

                                                                                £656 - £829 / week

                                                                                Book View

                                                                                from £120 / night

                                                                                Distance approx 18.17 miles from Chestertown

                                                                                  9

                                                                                  Cottage rental in Paradox

                                                                                  New York / Paradox

                                                                                  2 5 7 nights min

                                                                                  • 2 bedrooms
                                                                                  • sleeps 5
                                                                                  • 7 nights min
                                                                                  • Child friendly

                                                                                  from £133 / night

                                                                                  £931 / week

                                                                                  Book View

                                                                                  Responds fast!
                                                                                  avg. 3 hours 6 minutes

                                                                                  from £133 / night

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