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

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23 Holiday homes

(5) Excellent 

Certificate of Excellence

    28

    Holiday home with swimming pool in Chestertown

    Maryland / Chestertown

    4 8 2 nights min

    • 4 bedrooms
    • sleeps 8
    • 2 nights min
    • Nearest beach 5 km
    • Swimming pool
    • Child friendly

    Certificate of Excellence

    from £218 / night

    £1,220 / week

    Book View

    Responds fast!
    avg. 2 hours 21 minutes

    from £218 / night

    (3) Excellent 

      7

      Chestertown holiday cottage accommodation

      Maryland / Chestertown

      1 3 1 night min

      • 1 bedroom
      • sleeps 3
      • 1 night min
      • Air conditioning
      • Private garden

      from £169 / night

      £1,183 / week

      Book View

      from £169 / night

      (4) Very Good 

        11

        Holiday home in Chestertown

        Maryland / Chestertown

        3 7 2 nights min

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

        from £127 / night

        £819 - £1,002 / week

        Book View

        Responds fast!
        avg. 2 hours 41 minutes

        from £127 / night

        (3) Excellent 

          17

          Chestertown holiday home let

          Maryland / Chestertown

          1 3 1 night min

          • 1 bedroom
          • sleeps 3
          • 1 night min
          • Child friendly
          • Air conditioning
          • Pet friendly

          from £118 / night

          £697 / week

          Book View

          from £118 / night

          (3) Very Good 

            14

            Home rental in Chestertown

            Maryland / Chestertown

            3 8 2 nights min

            • 3 bedrooms
            • sleeps 8
            • 2 nights min
            • Child friendly
            • Air conditioning
            • Private garden

            from £257 / night

            £1,738 / week

            Book View

            from £257 / night

            (2) Very Good 

              16

              Chestertown holiday home rental

              Maryland / Chestertown

              4 8 2 nights min

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

              from £566 / night

              £3,484 / week

              Book View

              from £566 / night

              (1) Excellent 

                22

                Holiday home in Chestertown

                Maryland / Chestertown

                2 5 3 nights min

                • 2 bedrooms
                • sleeps 5
                • 3 nights min
                • Beach / lakeside relaxation
                • Child friendly
                • Air conditioning

                from £127 / night

                £784 / week

                Book View

                Responds fast!
                avg. 3 hours 2 minutes

                from £127 / night

                (1) Excellent 

                  7

                  Holiday apartment in Chestertown

                  Maryland / Chestertown

                  1 2 1 night min

                  • 1 bedroom
                  • sleeps 2
                  • 1 night min
                  • Child friendly
                  • Air conditioning

                  from £77 / night

                  £537 / week

                  Book View

                  Responds fast!
                  avg. 3 hours 2 minutes

                  from £77 / night

                  (7) Excellent 

                    10

                    Chestertown holiday apartment rental

                    Maryland / Chestertown

                    1 2 3 nights min

                    • 1 bedroom
                    • sleeps 2
                    • 3 nights min
                    • Nearest beach 24 km
                    • Child friendly
                    • Air conditioning

                    from £87 / night

                    £597 / week

                    Book View

                    Responds fast!
                    avg. 3 hours 2 minutes

                    from £87 / night

                    Great rentals within 20 miles that match your search

                    Distance approx 10.9 miles from Chestertown Show on Map

                    (1) Excellent 

                      10

                      Holiday bungalow in Rock Hall

                      Maryland / Rock Hall

                      3 8 2 nights min

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

                      from £249 / night

                      £1,738 / week

                      Book View

                      from £249 / night

                      Distance approx 18.6 miles from Chestertown

                        26

                        Stevensville holiday home rental

                        Kent Island / Stevensville

                        3 10 3 nights min

                        • 3 bedrooms
                        • sleeps 10
                        • 3 nights min
                        • Beach / lakeside relaxation
                        • Child friendly
                        • Air conditioning

                        from £1,219 / night

                        £6,094 / week

                        Book View

                        from £1,219 / night

                        Distance approx 17.67 miles from Chestertown

                          13

                          Holiday apartment in Centreville

                          Maryland / Centreville

                          1 3 1 night min

                          • 1 bedroom
                          • sleeps 3
                          • 1 night min
                          • Air conditioning
                          • Private garden

                          from £102 / night

                          £714 / week

                          Book View

                          from £102 / night

                          Distance approx 7.52 miles from Chestertown

                          (2) Very Good 

                            39

                            Still Pond holiday home rental

                            Maryland / Still Pond

                            1 3 1 night min

                            • 1 bedroom
                            • sleeps 3
                            • 1 night min
                            • Nearest beach 5 km
                            • Child friendly
                            • Air conditioning

                            from £48 / night

                            £350 / week

                            Book View

                            Responds fast!
                            avg. 2 hours 10 minutes

                            from £48 / night

                            Distance approx 10.97 miles from Chestertown Show on Map

                              8

                              Rock Hall holiday home rental

                              Maryland / Rock Hall

                              2 5 2 nights min

                              • 2 bedrooms
                              • sleeps 5
                              • 2 nights min
                              • Child friendly
                              • Air conditioning
                              • Pet friendly

                              from £217 / night

                              £1,516 / week

                              Book View

                              Responds fast!
                              avg. 3 hours 15 minutes

                              from £217 / night

                              Distance approx 7.52 miles from Chestertown

                                58

                                Holiday home in Still Pond

                                Maryland / Still Pond

                                2 6 1 night min

                                • 2 bedrooms
                                • sleeps 6
                                • 1 night min
                                • Nearest beach 5 km
                                • Child friendly
                                • Air conditioning

                                from £48 / night

                                £336 / week

                                Book View

                                Responds fast!
                                avg. 2 hours 10 minutes

                                from £48 / night

                                Distance approx 10.7 miles from Chestertown Show on Map

                                (3) Excellent 

                                  12

                                  Rock Hall holiday home rental

                                  Maryland / Rock Hall

                                  3 10 2 nights min

                                  • 3 bedrooms
                                  • sleeps 10
                                  • 2 nights min
                                  • Child friendly
                                  • Pet friendly

                                  from £297 / night

                                  £1,866 / week

                                  Book View

                                  Responds fast!
                                  avg. 3 hours 15 minutes

                                  from £297 / night

                                  Distance approx 18.02 miles from Chestertown Show on Map

                                  (14) Excellent 

                                    19

                                    Holiday home rental

                                    Maryland / Kent Island

                                    3 12 3 nights min

                                    • 3 bedrooms
                                    • sleeps 12
                                    • 3 nights min
                                    • Beach / lakeside relaxation
                                    • Nearest beach 5 km
                                    • Child friendly

                                    from £218 / night

                                    £1,220 - £2,178 / week

                                    Book View

                                    from £218 / night

                                    Distance approx 18.76 miles from Chestertown

                                      11

                                      Holiday apartment in Stevensville

                                      Kent Island / Stevensville

                                      2 6 2 nights min

                                      • 2 bedrooms
                                      • sleeps 6
                                      • 2 nights min
                                      • Child friendly

                                      from £287 / night

                                      £1,704 / week

                                      Book View

                                      from £287 / night

                                      Distance approx 19.14 miles from Chestertown

                                        15

                                        Wye Mills holiday apartment rental

                                        Talbot County / Wye Mills

                                        1 5 1 night min

                                        • 1 bedroom
                                        • sleeps 5
                                        • 1 night min
                                        • Child friendly
                                        • Air conditioning
                                        • Pet friendly

                                        from £121 / night

                                        £848 / week

                                        Book View

                                        from £121 / night

                                        Distance approx 10.71 miles from Chestertown Show on Map

                                          45

                                          Holiday home in Rock Hall

                                          Maryland / Rock Hall

                                          1 3 1 night min

                                          • 1 bedroom
                                          • sleeps 3
                                          • 1 night min
                                          • Child friendly

                                          from £35 / night

                                          £223 - £446 / week

                                          Book View

                                          Responds fast!
                                          avg. 2 hours 10 minutes

                                          from £35 / night

                                          Distance approx 10.71 miles from Chestertown Show on Map

                                            88

                                            Holiday home in Rock Hall

                                            Maryland / Rock Hall

                                            4 7 1 night min

                                            • 4 bedrooms
                                            • sleeps 7
                                            • 1 night min
                                            • Child friendly

                                            from £87 / night

                                            £562 - £2,038 / week

                                            Book View

                                            Responds fast!
                                            avg. 2 hours 10 minutes

                                            from £87 / night

                                            Distance approx 11.02 miles from Chestertown Show on Map

                                              12

                                              Holiday home in Rock Hall

                                              Maryland / Rock Hall

                                              3 6 min stay varies

                                              • 3 bedrooms
                                              • sleeps 6
                                              • min stay varies
                                              • Child friendly
                                              • Air conditioning
                                              • Pet friendly

                                              from £182 / night

                                              £1,273 / week

                                              Book View

                                              Responds fast!
                                              avg. 3 hours 15 minutes

                                              from £182 / night

                                              Distance approx 10.71 miles from Chestertown Show on Map

                                                53

                                                Holiday home in Rock Hall

                                                Maryland / Rock Hall

                                                1 3 1 night min

                                                • 1 bedroom
                                                • sleeps 3
                                                • 1 night min
                                                • Nearest beach 2 km
                                                • Child friendly
                                                • Air conditioning

                                                from £35 / night

                                                £225 - £450 / week

                                                Book View

                                                Responds fast!
                                                avg. 2 hours 10 minutes

                                                from £35 / night

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