Houses in Bailey Island – Holiday Lettings - Holiday Rentals Bailey Island

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114 Holiday homes

    26

    Holiday home in Bailey Island

    Maine / Bailey Island

    7 14 7 nights min

    • 7 bedrooms
    • sleeps 14
    • 7 nights min
    • Child friendly

    from £429 / night

    £3,001 / week

    Book View

    from £429 / night

      28

      Bailey Island holiday home rental

      Maine / Bailey Island

      3 10 7 nights min

      • 3 bedrooms
      • sleeps 10
      • 7 nights min
      • Child friendly
      • Private garden

      from £453 / night

      £3,171 / week

      Book View

      from £453 / night

      Great rentals within 20 miles that match your search

      Distance approx 6.92 miles from Bailey Island

      (4) Excellent 

        29

        Holiday home in Phippsburg

        Mid Coast Maine / Phippsburg

        3 8 7 nights min

        • 3 bedrooms
        • sleeps 8
        • 7 nights min
        • Child friendly
        • Pet friendly
        • Private garden

        from £170 / night

        £1,190 / week

        Book View

        from £170 / night

        Distance approx 18.02 miles from Bailey Island

        (3) Very Good 

          12

          Holiday apartment in Cape Elizabeth

          Maine / Cape Elizabeth

          2 6 2 nights min

          • 2 bedrooms
          • sleeps 6
          • 2 nights min
          • Beach / lakeside relaxation
          • Nearest beach 0.2 km
          • Child friendly

          from £169 / night

          £1,241 - £2,482 / week

          Book View

          from £169 / night

          Distance approx 17.76 miles from Bailey Island

            26

            Southport holiday home rental

            Mid Coast Maine / Southport

            3 6 min stay varies

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

            from £247 / night

            £1,729 - £2,981 / week

            Enquire View

            from £247 / night

            Distance approx 12.83 miles from Bailey Island

            (2) Very Good 

              17

              Brunswick holiday apartment rental

              Mid Coast Maine / Brunswick

              2 3 4 nights min

              • 2 bedrooms
              • sleeps 3
              • 4 nights min
              • Nearest beach 10 km
              • Air conditioning

              from £85 / night

              £554 / week

              Book View

              Responds fast!
              avg. 2 hours 11 minutes

              from £85 / night

              Distance approx 18.66 miles from Bailey Island

                17

                Southport holiday home rental

                Mid Coast Maine / Southport

                3 6 min stay varies

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

                from £150 / night

                £1,046 - £1,832 / week

                Enquire View

                from £150 / night

                Distance approx 17.29 miles from Bailey Island

                  17

                  Holiday home rental

                  Southport / Newagen

                  3 6 min stay varies

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

                  from £175 / night

                  £1,220 - £2,136 / week

                  Enquire View

                  from £175 / night

                  Distance approx 19 miles from Bailey Island

                    15

                    Holiday home in Windham

                    Maine / Windham

                    3 8 7 nights min

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

                    from £235 / night

                    £1,640 / week

                    Book View

                    from £235 / night

                    Distance approx 16.86 miles from Bailey Island

                      21

                      Holiday home in Southport

                      Mid Coast Maine / Southport

                      3 6 min stay varies

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

                      from £278 / night

                      £1,941 - £3,387 / week

                      Enquire View

                      from £278 / night

                      Distance approx 17.43 miles from Bailey Island

                        9

                        Holiday home in Southport

                        Mid Coast Maine / Southport

                        2 4 14 nights min

                        • 2 bedrooms
                        • sleeps 4
                        • 14 nights min
                        • Ask owner if suitable for children
                        • Pet friendly

                        from £128 / night

                        £891 / week

                        Enquire View

                        from £128 / night

                        Distance approx 10.46 miles from Bailey Island

                          42

                          Falmouth holiday home rental

                          Maine / Falmouth

                          3 6 2 nights min

                          • 3 bedrooms
                          • sleeps 6
                          • 2 nights min
                          • Beach / lakeside relaxation
                          • Child friendly
                          • Car not necessary

                          from £427 / night

                          £2,308 / week

                          Book View

                          Responds fast!
                          avg. 2 hours 40 minutes

                          from £427 / night

                          Distance approx 11.1 miles from Bailey Island

                          (2) Average 

                            23

                            Holiday home in West Bath

                            Mid Coast Maine / West Bath

                            3 8 7 nights min

                            • 3 bedrooms
                            • sleeps 8
                            • 7 nights min
                            • Beach / lakeside relaxation
                            • Nearest beach 0 km
                            • Child friendly

                            from £124 / night

                            £863 - £2,244 / week

                            Book View

                            from £124 / night

                            Distance approx 7.76 miles from Bailey Island

                            (1) Excellent 

                              23

                              Freeport holiday home rental

                              Maine / Freeport

                              4 8 7 nights min

                              • 4 bedrooms
                              • sleeps 8
                              • 7 nights min
                              • Beach / lakeside relaxation
                              • Child friendly
                              • Private garden

                              from £364 / night

                              £2,546 / week

                              Book View

                              from £364 / night

                              Distance approx 13.71 miles from Bailey Island

                                9

                                Holiday apartment in South Portland

                                Maine / South Portland

                                2 4 2 nights min

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

                                from £108 / night

                                £561 / week

                                Book View

                                from £108 / night

                                Distance approx 15.82 miles from Bailey Island

                                  23

                                  Holiday home in Georgetown

                                  Mid Coast Maine / Georgetown

                                  4 7 7 nights min

                                  • 4 bedrooms
                                  • sleeps 7
                                  • 7 nights min
                                  • Child friendly

                                  from £244 / night

                                  £1,704 / week

                                  Book View

                                  from £244 / night

                                  Distance approx 10.48 miles from Bailey Island

                                    6

                                    Holiday home rental

                                    Maine / Yarmouth

                                    2 4 2 nights min

                                    • 2 bedrooms
                                    • sleeps 4
                                    • 2 nights min
                                    • Nearest beach 3 km
                                    • Child friendly
                                    • Air conditioning

                                    from £113 / night

                                    £629 / week

                                    Book View

                                    Responds fast!
                                    avg. 3 hours 37 minutes

                                    from £113 / night

                                    Distance approx 12.82 miles from Bailey Island

                                      23

                                      Holiday home in Georgetown

                                      Mid Coast Maine / Georgetown

                                      2 4 min stay varies

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

                                      from £192 / night

                                      £1,340 - £2,342 / week

                                      Enquire View

                                      from £192 / night

                                      Distance approx 12.85 miles from Bailey Island

                                      (3) Excellent 

                                        72

                                        Home letting in South Portland

                                        Maine / South Portland

                                        3 9 min stay varies

                                        • 3 bedrooms
                                        • sleeps 9
                                        • min stay varies
                                        • Child friendly
                                        • Air conditioning
                                        • Pet friendly

                                        from £255 / night

                                        £1,618 - £4,276 / week

                                        Book View

                                        Responds fast!
                                        avg. 2 hours 40 minutes

                                        from £255 / night

                                        Distance approx 12.86 miles from Bailey Island

                                        (3) Excellent 

                                          12

                                          Brunswick holiday apartment let

                                          Mid Coast Maine / Brunswick

                                          1 2 7 nights min

                                          • 1 bedroom
                                          • sleeps 2
                                          • 7 nights min
                                          • Nearest beach 30 km
                                          • Air conditioning
                                          • Pet friendly

                                          from £71 / night

                                          £439 / week

                                          Book View

                                          Responds fast!
                                          avg. 2 hours 11 minutes

                                          from £71 / night

                                          Distance approx 17.29 miles from Bailey Island

                                            17

                                            Holiday home in Southport

                                            Mid Coast Maine / Southport

                                            2 4 min stay varies

                                            • 2 bedrooms
                                            • sleeps 4
                                            • min stay varies
                                            • Child friendly
                                            • Pet friendly

                                            from £207 / night

                                            £1,447 - £2,537 / week

                                            Enquire View

                                            from £207 / night

                                            Distance approx 13.02 miles from Bailey Island

                                              19

                                              Holiday home in Georgetown

                                              Mid Coast Maine / Georgetown

                                              2 6 min stay varies

                                              • 2 bedrooms
                                              • sleeps 6
                                              • min stay varies
                                              • Child friendly

                                              from £192 / night

                                              £1,340 - £2,342 / week

                                              Enquire View

                                              from £192 / night

                                              Distance approx 8.48 miles from Bailey Island

                                                24

                                                South Freeport holiday cottage rental

                                                Maine / South Freeport

                                                2 6 min stay varies

                                                • 2 bedrooms
                                                • sleeps 6
                                                • min stay varies
                                                • Child friendly

                                                from £222 / night

                                                £1,552 / week

                                                Book View

                                                Responds fast!
                                                avg. 13 minutes

                                                from £222 / night

                                                Distance approx 18.62 miles from Bailey Island

                                                  31

                                                  Boothbay Harbor holiday home rental

                                                  Mid Coast Maine / Boothbay Harbor

                                                  4 5 7 nights min

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

                                                  from £432 / night

                                                  £3,020 / week

                                                  Book View

                                                  from £432 / night

                                                  Distance approx 14.61 miles from Bailey Island

                                                  (1) Excellent 

                                                    13

                                                    Holiday home in Georgetown

                                                    Mid Coast Maine / Georgetown

                                                    4 9 7 nights min

                                                    • 4 bedrooms
                                                    • sleeps 9
                                                    • 7 nights min
                                                    • Ask owner if suitable for children
                                                    • Ask about pets

                                                    from £760 / night

                                                    £5,319 / week

                                                    Book View

                                                    from £760 / night

                                                    Distance approx 3.21 miles from Bailey Island

                                                      9

                                                      Cottage rental in Orrs Island

                                                      Maine / Orrs Island

                                                      3 7 3 nights min

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

                                                      from £241 / night

                                                      £1,685 / week

                                                      Book View

                                                      from £241 / night

                                                      Distance approx 16.83 miles from Bailey Island

                                                        24

                                                        Westbrook ski apartment to rent.

                                                        Maine / Westbrook

                                                        1 6 min stay varies

                                                        • 1 bedroom
                                                        • sleeps 6
                                                        • min stay varies
                                                        • Ski
                                                        • Child friendly
                                                        • Air conditioning

                                                        from £51 / night

                                                        £357 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 36 minutes

                                                        from £51 / night

                                                        Distance approx 19.16 miles from Bailey Island

                                                        (3) Very Good 

                                                          31

                                                          Holiday home in Boothbay

                                                          Mid Coast Maine / Boothbay

                                                          4 10 min stay varies

                                                          • 4 bedrooms
                                                          • sleeps 10
                                                          • min stay varies
                                                          • Child friendly
                                                          • Pet friendly

                                                          from £230 / night

                                                          £1,605 - £2,808 / week

                                                          Enquire View

                                                          from £230 / night

                                                          Distance approx 16.83 miles from Bailey Island

                                                            24

                                                            Westbrook ski apartment to rent.

                                                            Maine / Westbrook

                                                            1 6 min stay varies

                                                            • 1 bedroom
                                                            • sleeps 6
                                                            • min stay varies
                                                            • Ski
                                                            • Child friendly
                                                            • Air conditioning

                                                            from £53 / night

                                                            £367 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 9 minutes

                                                            from £53 / night

                                                            Distance approx 19.5 miles from Bailey Island

                                                              46

                                                              Holiday home letting

                                                              Mid Coast Maine / Boothbay Harbor

                                                              4 7 min stay varies

                                                              • 4 bedrooms
                                                              • sleeps 7
                                                              • min stay varies
                                                              • Child friendly

                                                              from £216 / night

                                                              £1,683 / week

                                                              Book View

                                                              from £216 / night

                                                              Distance approx 18.62 miles from Bailey Island

                                                                17

                                                                Boothbay Harbor holiday farmhouse rental

                                                                Mid Coast Maine / Boothbay Harbor

                                                                4 5 7 nights min

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

                                                                from £432 / night

                                                                £3,020 / week

                                                                Book View

                                                                from £432 / night

                                                                Distance approx 13.1 miles from Bailey Island

                                                                  71

                                                                  Holiday home in Portland

                                                                  Maine / Portland

                                                                  4 9 min stay varies

                                                                  • 4 bedrooms
                                                                  • sleeps 9
                                                                  • min stay varies
                                                                  • Nearest beach 0 km
                                                                  • Child friendly

                                                                  from £439 / night

                                                                  £2,638 - £5,740 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 2 hours 40 minutes

                                                                  from £439 / night

                                                                  Distance approx 7.06 miles from Bailey Island

                                                                    12

                                                                    Harpswell holiday home rental

                                                                    Mid Coast Maine / Harpswell

                                                                    2 4 min stay varies

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

                                                                    from £103 / night

                                                                    £718 - £1,256 / week

                                                                    Enquire View

                                                                    from £103 / night

                                                                    Distance approx 13.23 miles from Bailey Island

                                                                      4

                                                                      Holiday apartment in Portland

                                                                      Maine / Portland

                                                                      2 4 30 nights min

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

                                                                      from £87 / night

                                                                      £604 - £2,416 / week

                                                                      Book View

                                                                      from £87 / night

                                                                      Distance approx 18.68 miles from Bailey Island

                                                                        36

                                                                        Holiday home letting

                                                                        Maine / Capitol Island

                                                                        4 7 min stay varies

                                                                        • 4 bedrooms
                                                                        • sleeps 7
                                                                        • min stay varies
                                                                        • Child friendly

                                                                        from £197 / night

                                                                        £1,510 / week

                                                                        Book View

                                                                        from £197 / night

                                                                        Distance approx 14.46 miles from Bailey Island

                                                                        (1) Excellent 

                                                                          6

                                                                          Home letting in Portland

                                                                          Maine / Portland

                                                                          1 2 3 nights min

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

                                                                          from £153 / night

                                                                          £1,069 / week

                                                                          Book View

                                                                          from £153 / night

                                                                          Distance approx 10.61 miles from Bailey Island

                                                                            29

                                                                            Holiday cottage in Phippsburg

                                                                            Mid Coast Maine / Phippsburg

                                                                            2 8 7 nights min

                                                                            • 2 bedrooms
                                                                            • sleeps 8
                                                                            • 7 nights min
                                                                            • Child friendly
                                                                            • Pet friendly

                                                                            from £317 / night

                                                                            £2,217 / week

                                                                            Book View

                                                                            from £317 / night

                                                                            Distance approx 11.3 miles from Bailey Island

                                                                              14

                                                                              Holiday apartment in Freeport

                                                                              Maine / Freeport

                                                                              2 5 2 nights min

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

                                                                              from £111 / night

                                                                              £887 - £1,011 / week

                                                                              Book View

                                                                              from £111 / night

                                                                              Distance approx 13.7 miles from Bailey Island

                                                                                25

                                                                                Ski apartment to rent in Portland

                                                                                Maine / Portland

                                                                                3 4 2 nights min

                                                                                • 3 bedrooms
                                                                                • sleeps 4
                                                                                • 2 nights min
                                                                                • Ski
                                                                                • Child friendly
                                                                                • Air conditioning

                                                                                from £83 / night

                                                                                £580 / week

                                                                                Book View

                                                                                Responds fast!
                                                                                avg. 2 hours 32 minutes

                                                                                from £83 / night

                                                                                Distance approx 7.99 miles from Bailey Island

                                                                                  24

                                                                                  Long Island holiday home rental

                                                                                  Maine / Long Island

                                                                                  2 6 3 nights min

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

                                                                                  from £311 / night

                                                                                  £2,175 / week

                                                                                  Book View

                                                                                  from £311 / night

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