Holiday Houses in Annapolis

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75 Holiday homes

    26

    Maryland / Annapolis

    5 20 2 nights min

    • 5 bedrooms
    • sleeps 20
    • 2 nights min
    • Beach / lakeside relaxation
    • Nearest beach 0.2 km
    • Child friendly

    from £632 / night

    £2,729 - £3,493 / week

    Book View

    from £632 / night

    (1) Excellent 

      56

      Maryland / Annapolis

      4 11 5 nights min

      • 4 bedrooms
      • sleeps 11
      • 5 nights min
      • Nearest beach 0.5 km
      • Child friendly
      • Pet friendly

      from £455 / night

      £3,184 / week

      Book View

      from £455 / night

      (2) Excellent 

        10

        Maryland / Annapolis

        1 2 1 night min

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

        from £54 / night

        £376 / week

        Book View

        from £54 / night

          21

          Maryland / Annapolis

          5 11 min stay varies

          • 5 bedrooms
          • sleeps 11
          • min stay varies
          • Beach / lakeside relaxation
          • Nearest beach 0.1 km
          • Child friendly

          from £431 / night

          £3,173 - £5,257 / week

          Book View

          from £431 / night

          (20) Excellent 

            25

            Maryland / Annapolis

            3 6 2 nights min

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

            from £291 / night

            £1,637 / week

            Book View

            Responds fast!
            avg. 2 hours 12 minutes

            from £291 / night

            (1) Excellent 

              17

              Maryland / Annapolis

              3 7 2 nights min

              • 3 bedrooms
              • sleeps 7
              • 2 nights min
              • Child friendly
              • Air conditioning
              • Pet friendly

              from £260 / night

              £2,092 / week

              Book View

              Responds fast!
              avg. 46 minutes

              from £260 / night

                7

                Maryland / Annapolis

                1 2 1 night min

                • 1 bedroom
                • sleeps 2
                • 1 night min
                • Ask about pets

                from £273 / night

                £1,001 / week

                Book View

                from £273 / night

                (6) Excellent 

                  19

                  Maryland / Annapolis

                  6 12 min stay varies

                  • 6 bedrooms
                  • sleeps 12
                  • min stay varies
                  • Child friendly
                  • Air conditioning

                  from £683 / night

                  £4,548 - £9,095 / week

                  Book View

                  Responds fast!
                  avg. 1 hour 17 minutes

                  from £683 / night

                  (2) Excellent 

                    52

                    Maryland / Annapolis

                    3 6 2 nights min

                    • 3 bedrooms
                    • sleeps 6
                    • 2 nights min
                    • Nearest beach 6 km
                    • Child friendly
                    • Car not necessary

                    from £228 / night

                    £909 - £1,036 / week

                    Book View

                    Responds fast!
                    avg. 27 minutes

                    from £228 / night

                      15

                      Maryland / Annapolis

                      2 5 min stay varies

                      • 2 bedrooms
                      • sleeps 5
                      • min stay varies
                      • Car not necessary
                      • Air conditioning
                      • Private garden

                      from £228 / night

                      £2,274 / week

                      Book View

                      from £228 / night

                        25

                        Maryland / Annapolis

                        1 4 min stay varies

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

                        from £81 / night

                        £567 / week

                        Book View

                        Responds fast!
                        avg. 32 minutes

                        from £81 / night

                          4

                          Maryland / Annapolis

                          4 10 2 nights min

                          • 4 bedrooms
                          • sleeps 10
                          • 2 nights min
                          • Child friendly

                          from £451 / night

                          £2,729 / week

                          Book View

                          from £451 / night

                            23

                            Maryland / Annapolis

                            3 8 5 nights min

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

                            from £273 / night

                            £1,819 / week

                            Book View

                            from £273 / night

                              24

                              Maryland / Annapolis

                              3 6 3 nights min

                              • 3 bedrooms
                              • sleeps 6
                              • 3 nights min
                              • Ask owner if suitable for children
                              • Air conditioning

                              from £341 / night

                              £2,388 / week

                              Book View

                              from £341 / night

                                30

                                Maryland / Annapolis

                                3 6 min stay varies

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

                                from £409 / night

                                £2,859 / week

                                Book View

                                Responds fast!
                                avg. 25 minutes

                                from £409 / night

                                (3) Very Good 

                                  30

                                  Maryland / Annapolis

                                  4 9 1 night min

                                  • 4 bedrooms
                                  • sleeps 9
                                  • 1 night min
                                  • Child friendly
                                  • Air conditioning
                                  • Ask about pets

                                  from £386 / night

                                  £2,266 - £2,932 / week

                                  Book View

                                  from £386 / night

                                    15

                                    Maryland / Annapolis

                                    3 8 1 night min

                                    • 3 bedrooms
                                    • sleeps 8
                                    • 1 night min
                                    • Air conditioning
                                    • Private garden

                                    from £384 / night

                                    £2,687 / week

                                    Book View

                                    from £384 / night

                                      43

                                      Maryland / Annapolis

                                      5 11 min stay varies

                                      • 5 bedrooms
                                      • sleeps 11
                                      • min stay varies
                                      • Swimming pool
                                      • Child friendly
                                      • Air conditioning

                                      from £660 / night

                                      £4,616 / week

                                      Book View

                                      Responds fast!
                                      avg. 25 minutes

                                      from £660 / night

                                      (1) Excellent 

                                        18

                                        Maryland / Annapolis

                                        3 11 2 nights min

                                        • 3 bedrooms
                                        • sleeps 11
                                        • 2 nights min
                                        • Ask owner if suitable for children
                                        • Air conditioning
                                        • Private garden

                                        from £632 / night

                                        £4,912 / week

                                        Book View

                                        from £632 / night

                                          24

                                          Maryland / Annapolis

                                          3 6 min stay varies

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

                                          from £123 / night

                                          £860 / week

                                          Book View

                                          Responds fast!
                                          avg. 25 minutes

                                          from £123 / night

                                            24

                                            Maryland / Annapolis

                                            4 10 min stay varies

                                            • 4 bedrooms
                                            • sleeps 10
                                            • min stay varies
                                            • Child friendly
                                            • Air conditioning

                                            from £291 / night

                                            £2,031 / week

                                            Book View

                                            Responds fast!
                                            avg. 25 minutes

                                            from £291 / night

                                            (1)  

                                              7

                                              Maryland / Annapolis

                                              3 8 3 nights min

                                              • 3 bedrooms
                                              • sleeps 8
                                              • 3 nights min
                                              • Child friendly
                                              • Car not necessary
                                              • Ask about pets

                                              from £410 / night

                                              £3,547 / week

                                              Book View

                                              from £410 / night

                                              Great rentals within 20 miles that match your search

                                              Distance approx 28.04 km from Annapolis

                                              (3) Excellent 

                                                12

                                                Maryland / Rock Hall

                                                3 10 2 nights min

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

                                                from £307 / night

                                                £1,934 / week

                                                Book View

                                                Responds fast!
                                                avg. 3 hours 15 minutes

                                                from £307 / night

                                                Distance approx 28.26 km from Annapolis

                                                  11

                                                  Calvert County / North Beach

                                                  3 8 1 night min

                                                  • 3 bedrooms
                                                  • sleeps 8
                                                  • 1 night min
                                                  • Child friendly
                                                  • Air conditioning
                                                  • Pet friendly

                                                  from £454 / night

                                                  £3,173 / week

                                                  Book View

                                                  from £454 / night

                                                  Distance approx 27.59 km from Annapolis

                                                    12

                                                    Maryland / Rock Hall

                                                    3 6 min stay varies

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

                                                    from £114 / night

                                                    £793 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 3 hours 15 minutes

                                                    from £114 / night

                                                    Distance approx 30.4 km from Annapolis

                                                    (1) Average 

                                                      38

                                                      Talbot County / St. Michaels

                                                      6 12 2 nights min

                                                      • 6 bedrooms
                                                      • sleeps 12
                                                      • 2 nights min
                                                      • Beach / lakeside relaxation
                                                      • Nearest beach 7 km
                                                      • Swimming pool

                                                      from £910 / night

                                                      £5,639 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 3 hours 35 minutes

                                                      from £910 / night

                                                      Distance approx 25.85 km from Annapolis

                                                        9

                                                        Maryland / Bowie

                                                        2 6 2 nights min

                                                        • 2 bedrooms
                                                        • sleeps 6
                                                        • 2 nights min
                                                        • Child friendly
                                                        • Air conditioning
                                                        • Private garden

                                                        from £132 / night

                                                        £924 / week

                                                        Book View

                                                        from £132 / night

                                                        Distance approx 20.38 km from Annapolis Show on Map

                                                          24

                                                          Maryland / Pasadena

                                                          2 4 min stay varies

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

                                                          from £80 / night

                                                          £561 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 26 minutes

                                                          from £80 / night

                                                          Distance approx 16.26 km from Annapolis Show on Map

                                                          (3) Excellent 

                                                            21

                                                            Kent Island / Chester

                                                            4 8 min stay varies

                                                            • 4 bedrooms
                                                            • sleeps 8
                                                            • min stay varies
                                                            • Beach / lakeside relaxation
                                                            • Nearest beach 14 km
                                                            • Child friendly

                                                            from £260 / night

                                                            £1,815 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 2 hours 24 minutes

                                                            from £260 / night

                                                            Distance approx 14.75 km from Annapolis Show on Map

                                                              52

                                                              Maryland / Severna Park

                                                              4 13 2 nights min

                                                              • 4 bedrooms
                                                              • sleeps 13
                                                              • 2 nights min
                                                              • Child friendly
                                                              • Air conditioning
                                                              • Private garden

                                                              from £181 / night

                                                              £1,267 / week

                                                              Book View

                                                              from £181 / night

                                                              Distance approx 20.03 km from Annapolis Show on Map

                                                                15

                                                                Maryland / Glen Burnie

                                                                1 2 3 nights min

                                                                • 1 bedroom
                                                                • sleeps 2
                                                                • 3 nights min
                                                                • Child friendly
                                                                • Air conditioning
                                                                • Private garden

                                                                from £91 / night

                                                                £637 / week

                                                                Book View

                                                                from £91 / night

                                                                Distance approx 31.86 km from Annapolis

                                                                  7

                                                                  Talbot County / St. Michaels

                                                                  2 4 2 nights min

                                                                  • 2 bedrooms
                                                                  • sleeps 4
                                                                  • 2 nights min
                                                                  • Child friendly
                                                                  • Air conditioning
                                                                  • Private garden

                                                                  from £351 / night

                                                                  £2,001 / week

                                                                  Book View

                                                                  from £351 / night

                                                                  Distance approx 29.95 km from Annapolis

                                                                    33

                                                                    Maryland / Bowie

                                                                    5 16 3 nights min

                                                                    • 5 bedrooms
                                                                    • sleeps 16
                                                                    • 3 nights min
                                                                    • Child friendly
                                                                    • Air conditioning

                                                                    from £446 / night

                                                                    £3,120 - £3,757 / week

                                                                    Book View

                                                                    from £446 / night

                                                                    Distance approx 31.35 km from Annapolis

                                                                    (10) Very Good 

                                                                    Certificate of Excellence

                                                                      23

                                                                      Talbot County / St. Michaels

                                                                      2 5 min stay varies

                                                                      • 2 bedrooms
                                                                      • sleeps 5
                                                                      • min stay varies
                                                                      • Child friendly
                                                                      • Air conditioning
                                                                      • Pet friendly

                                                                      Certificate of Excellence

                                                                      from £196 / night

                                                                      £1,524 - £1,737 / week

                                                                      Book View

                                                                      Responds fast!
                                                                      avg. 2 hours 58 minutes

                                                                      from £196 / night

                                                                      Distance approx 18.96 km from Annapolis Show on Map

                                                                        6

                                                                        Maryland / Gambrills

                                                                        1 2 60 nights min

                                                                        • 1 bedroom
                                                                        • sleeps 2
                                                                        • 60 nights min
                                                                        • Air conditioning

                                                                        from £55 / night

                                                                        £344 / week

                                                                        Book View

                                                                        from £55 / night

                                                                        Distance approx 31.86 km from Annapolis

                                                                        (5) Excellent 

                                                                          22

                                                                          Talbot County / St. Michaels

                                                                          4 10 min stay varies

                                                                          • 4 bedrooms
                                                                          • sleeps 10
                                                                          • min stay varies
                                                                          • Beach / lakeside relaxation
                                                                          • Swimming pool
                                                                          • Child friendly

                                                                          from £455 / night

                                                                          £4,366 / week

                                                                          Book View

                                                                          from £455 / night

                                                                          Distance approx 28.47 km from Annapolis

                                                                          (1) Excellent 

                                                                            8

                                                                            Maryland / Baltimore

                                                                            2 4 59 nights min

                                                                            • 2 bedrooms
                                                                            • sleeps 4
                                                                            • 59 nights min
                                                                            • Child friendly
                                                                            • Air conditioning

                                                                            from £54 / night

                                                                            £376 / week

                                                                            Book View

                                                                            from £54 / night

                                                                            Distance approx 26.66 km from Annapolis

                                                                              19

                                                                              Maryland / Glen Burnie

                                                                              4 13 min stay varies

                                                                              • 4 bedrooms
                                                                              • sleeps 13
                                                                              • min stay varies
                                                                              • Child friendly
                                                                              • Air conditioning
                                                                              • Private garden

                                                                              from £137 / night

                                                                              £955 / week

                                                                              Book View

                                                                              from £137 / night

                                                                              Distance approx 31.39 km from Annapolis

                                                                              (14) Excellent 

                                                                                24

                                                                                Talbot County / St. Michaels

                                                                                2 5 min stay varies

                                                                                • 2 bedrooms
                                                                                • sleeps 5
                                                                                • min stay varies
                                                                                • Child friendly
                                                                                • Air conditioning
                                                                                • Pet friendly

                                                                                from £187 / night

                                                                                £1,433 - £1,647 / week

                                                                                Book View

                                                                                Responds fast!
                                                                                avg. 2 hours 58 minutes

                                                                                from £187 / night

                                                                                Distance approx 25.44 km from Annapolis

                                                                                (3) Very Good 

                                                                                  36

                                                                                  Talbot County / Wittman

                                                                                  5 10 min stay varies

                                                                                  • 5 bedrooms
                                                                                  • sleeps 10
                                                                                  • min stay varies
                                                                                  • Beach / lakeside relaxation
                                                                                  • Nearest beach 6 km
                                                                                  • Swimming pool

                                                                                  from £887 / night

                                                                                  £5,685 - £6,640 / week

                                                                                  Book View

                                                                                  from £887 / night