Apartments in Winter Harbor and Houses – Holiday Lettings - Holiday Rentals Winter Harbor

Close

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

443 Holiday homes

(46) Excellent 

Certificate of Excellence

    58

    Winter Harbor holiday home rental

    DownEast and Acadia Maine / Winter Harbor

    3 6 min stay varies

    • 3 bedrooms
    • sleeps 6
    • min stay varies
    • Nearest beach 0.2 km
    • Child friendly
    • Private garden

    Certificate of Excellence

    from £116 / night

    £789 - £975 / week

    Book View

    Responds fast!
    avg. 1 hour 9 minutes

    from £116 / night

    (2) Excellent 

      19

      Holiday cottage rental

      DownEast and Acadia Maine / Winter Harbor

      1 2 min stay varies

      • 1 bedroom
      • sleeps 2
      • min stay varies
      • Nearest beach 1 km
      • Private garden

      from £89 / night

      £621 / week

      Book View

      Responds fast!
      avg. 1 hour 17 minutes

      from £89 / night

        20

        Apartment rental in Winter Harbor with golf nearby

        DownEast and Acadia Maine / Winter Harbor

        1 2 min stay varies

        • 1 bedroom
        • sleeps 2
        • min stay varies
        • Nearest beach 1 km

        from £70 / night

        £484 / week

        Book View

        Responds fast!
        avg. 1 hour 17 minutes

        from £70 / night

          8

          Holiday apartment rental

          DownEast and Acadia Maine / Winter Harbor

          1 2 7 nights min

          • 1 bedroom
          • sleeps 2
          • 7 nights min
          • Child friendly
          • Pet friendly
          • Private garden

          from £129 / night

          £900 / week

          Book View

          from £129 / night

            9

            Holiday apartment in Winter Harbor

            DownEast and Acadia Maine / Winter Harbor

            1 2 5 nights min

            • 1 bedroom
            • sleeps 2
            • 5 nights min
            • Child friendly
            • Pet friendly

            from £129 / night

            £710 / week

            Book View

            from £129 / night

              10

              Holiday cottage in Winter Harbor

              DownEast and Acadia Maine / Winter Harbor

              2 5 7 nights min

              • 2 bedrooms
              • sleeps 5
              • 7 nights min
              • Nearest beach 3 km
              • Child friendly
              • Private garden

              from £137 / night

              £953 / week

              Book View

              from £137 / night

                22

                Holiday apartment rental

                DownEast and Acadia Maine / Winter Harbor

                1 2 min stay varies

                • 1 bedroom
                • sleeps 2
                • min stay varies
                • Nearest beach 1 km

                from £70 / night

                £484 / week

                Book View

                Responds fast!
                avg. 1 hour 17 minutes

                from £70 / night

                  9

                  Holiday home in Winter Harbor

                  DownEast and Acadia Maine / Winter Harbor

                  2 6 4 nights min

                  • 2 bedrooms
                  • sleeps 6
                  • 4 nights min
                  • Child friendly
                  • Private garden

                  from £178 / night

                  £1,241 / week

                  Book View

                  from £178 / night

                    24

                    Holiday log cabin rental

                    DownEast and Acadia Maine / Winter Harbor

                    3 6 4 nights min

                    • 3 bedrooms
                    • sleeps 6
                    • 4 nights min
                    • Child friendly
                    • Pet friendly

                    from £138 / night

                    £962 / week

                    Book View

                    Responds fast!
                    avg. 36 minutes

                    from £138 / night

                      15

                      Holiday home in Winter Harbor

                      DownEast and Acadia Maine / Winter Harbor

                      3 6 5 nights min

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

                      from £164 / night

                      £1,148 / week

                      Book View

                      from £164 / night

                      Great rentals within 20 miles that match your search

                      Distance approx 13.8 miles from Winter Harbor

                      (8) Excellent 

                      Certificate of Excellence

                        21

                        Home letting in Southwest Harbor with golf nearby

                        Mount Desert Island / Southwest Harbor

                        3 9 3 nights min

                        • 3 bedrooms
                        • sleeps 9
                        • 3 nights min
                        • Child friendly
                        • Private garden

                        Certificate of Excellence

                        from £142 / night

                        £798 - £1,330 / week

                        Book View

                        from £142 / night

                        Distance approx 6.02 miles from Winter Harbor

                          4

                          Holiday apartment with golf nearby in Bar Harbor

                          Mount Desert Island / Bar Harbor

                          1 4 min stay varies

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

                          from £120 / night

                          £444 - £1,578 / week

                          Book View

                          from £120 / night

                          Distance approx 13.64 miles from Winter Harbor

                          (1) Very Good 

                            30

                            Home rental in Franklin

                            DownEast and Acadia Maine / Franklin

                            3 6 min stay varies

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

                            from £125 / night

                            £869 / week

                            Book View

                            Responds fast!
                            avg. 19 minutes

                            from £125 / night

                            Distance approx 17.53 miles from Winter Harbor

                            (1) Excellent 

                              44

                              Tremont holiday home let

                              Mount Desert Island / Tremont

                              7 16 7 nights min

                              • 7 bedrooms
                              • sleeps 16
                              • 7 nights min
                              • Child friendly
                              • Private garden

                              from £520 / night

                              £3,635 - £5,408 / week

                              Book View

                              Responds fast!
                              avg. 1 hour 38 minutes

                              from £520 / night

                              Distance approx 17.53 miles from Winter Harbor

                              (1) Excellent 

                                15

                                Tremont holiday cottage rental

                                Mount Desert Island / Tremont

                                1 2 7 nights min

                                • 1 bedroom
                                • sleeps 2
                                • 7 nights min
                                • Private garden

                                from £173 / night

                                £1,210 / week

                                Book View

                                Responds fast!
                                avg. 1 hour 38 minutes

                                from £173 / night

                                Distance approx 13.97 miles from Winter Harbor

                                (1) Excellent 

                                  22

                                  Holiday home in Southwest Harbor

                                  Mount Desert Island / Southwest Harbor

                                  4 8 7 nights min

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

                                  from £342 / night

                                  £2,394 / week

                                  Book View

                                  from £342 / night

                                  Distance approx 11.01 miles from Winter Harbor

                                  (3) Excellent 

                                  Certificate of Excellence

                                    36

                                    Acadia National Park holiday home rental

                                    Mount Desert Island / Acadia National Park

                                    2 6 3 nights min

                                    • 2 bedrooms
                                    • sleeps 6
                                    • 3 nights min
                                    • Child friendly
                                    • Air conditioning
                                    • Pet friendly

                                    Certificate of Excellence

                                    from £111 / night

                                    £776 / week

                                    Book View

                                    from £111 / night

                                    Distance approx 8.97 miles from Winter Harbor

                                    (10) Very Good 

                                      15

                                      Cottage rental in Bar Harbor

                                      Mount Desert Island / Bar Harbor

                                      2 4 min stay varies

                                      • 2 bedrooms
                                      • sleeps 4
                                      • min stay varies
                                      • Beach / lakeside relaxation
                                      • Nearest beach 16 km
                                      • Child friendly

                                      from £178 / night

                                      £975 - £1,241 / week

                                      Book View

                                      Responds fast!
                                      avg. 2 hours 43 minutes

                                      from £178 / night

                                      Distance approx 9.57 miles from Winter Harbor

                                        16

                                        Bar Harbor holiday home rental

                                        Mount Desert Island / Bar Harbor

                                        4 8 7 nights min

                                        • 4 bedrooms
                                        • sleeps 8
                                        • 7 nights min
                                        • Child friendly
                                        • Car not necessary
                                        • Air conditioning

                                        from £187 / night

                                        £1,303 / week

                                        Book View

                                        from £187 / night

                                        Distance approx 14.66 miles from Winter Harbor

                                          5

                                          Holiday apartment rental

                                          Mount Desert Island / Southwest Harbor

                                          3 7 7 nights min

                                          • 3 bedrooms
                                          • sleeps 7
                                          • 7 nights min
                                          • Beach / lakeside relaxation
                                          • Swimming pool
                                          • Child friendly

                                          from £304 / night

                                          £2,128 / week

                                          Book View

                                          from £304 / night

                                          Distance approx 16.72 miles from Winter Harbor

                                            26

                                            Holiday cottage in Trenton

                                            DownEast and Acadia Maine / Trenton

                                            2 4 min stay varies

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

                                            from £200 / night

                                            £1,397 / week

                                            Book View

                                            Responds fast!
                                            avg. 19 minutes

                                            from £200 / night

                                            Distance approx 14.17 miles from Winter Harbor

                                            (1) Excellent 

                                              20

                                              Holiday home in Southwest Harbor

                                              Mount Desert Island / Southwest Harbor

                                              4 8 6 nights min

                                              • 4 bedrooms
                                              • sleeps 8
                                              • 6 nights min
                                              • Beach / lakeside relaxation
                                              • Child friendly
                                              • Ask about pets

                                              from £288 / night

                                              £1,773 / week

                                              Book View

                                              from £288 / night

                                              Distance approx 16.95 miles from Winter Harbor

                                              (35) Excellent 

                                              Certificate of Excellence

                                                20

                                                Holiday home in Acadia National Park

                                                Mount Desert Island / Acadia National Park

                                                3 6 min stay varies

                                                • 3 bedrooms
                                                • sleeps 6
                                                • min stay varies
                                                • Beach / lakeside relaxation
                                                • Child friendly
                                                • Private garden

                                                Certificate of Excellence

                                                from £151 / night

                                                £1,055 - £1,463 / week

                                                Book View

                                                from £151 / night

                                                Distance approx 14.45 miles from Winter Harbor

                                                (1) Excellent 

                                                  51

                                                  Holiday private room in Southwest Harbor

                                                  Mount Desert Island / Southwest Harbor

                                                  1 2 2 nights min

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

                                                  from £62 / night

                                                  £435 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 2 hours 16 minutes

                                                  from £62 / night

                                                  Distance approx 17.6 miles from Winter Harbor

                                                  (6) Excellent 

                                                    18

                                                    Holiday cottage in Southwest Harbor

                                                    Mount Desert Island / Southwest Harbor

                                                    3 5 7 nights min

                                                    • 3 bedrooms
                                                    • sleeps 5
                                                    • 7 nights min
                                                    • Beach / lakeside relaxation
                                                    • Child friendly

                                                    from £178 / night

                                                    £1,241 - £3,014 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 1 hour 51 minutes

                                                    from £178 / night

                                                    Distance approx 14.19 miles from Winter Harbor

                                                    (2) Excellent 

                                                      13

                                                      Holiday home in Bar Harbor

                                                      Mount Desert Island / Bar Harbor

                                                      4 8 7 nights min

                                                      • 4 bedrooms
                                                      • sleeps 8
                                                      • 7 nights min
                                                      • Child friendly
                                                      • Air conditioning
                                                      • Pet friendly

                                                      from £355 / night

                                                      £2,482 / week

                                                      Book View

                                                      from £355 / night

                                                      Distance approx 17.08 miles from Winter Harbor

                                                        24

                                                        Tremont holiday log cabin rental

                                                        Mount Desert Island / Tremont

                                                        1 5 min stay varies

                                                        • 1 bedroom
                                                        • sleeps 5
                                                        • min stay varies
                                                        • Child friendly
                                                        • Pet friendly

                                                        from £111 / night

                                                        £776 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 19 minutes

                                                        from £111 / night

                                                        Distance approx 11.88 miles from Winter Harbor

                                                          24

                                                          Holiday home in Bar Harbor

                                                          Mount Desert Island / Bar Harbor

                                                          4 8 7 nights min

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

                                                          from £355 / night

                                                          £2,349 / week

                                                          Book View

                                                          from £355 / night

                                                          Distance approx 14.9 miles from Winter Harbor

                                                            13

                                                            Holiday apartment in Southwest Harbor

                                                            Mount Desert Island / Southwest Harbor

                                                            2 4 7 nights min

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

                                                            from £200 / night

                                                            £1,397 / week

                                                            Book View

                                                            from £200 / night

                                                            Distance approx 7.42 miles from Winter Harbor

                                                              25

                                                              Ski home to rent in Sullivan

                                                              DownEast and Acadia Maine / Sullivan

                                                              4 12 min stay varies

                                                              • 4 bedrooms
                                                              • sleeps 12
                                                              • min stay varies
                                                              • Ski
                                                              • Child friendly

                                                              from £488 / night

                                                              £3,413 / week

                                                              Book View

                                                              Responds fast!
                                                              avg. 36 minutes

                                                              from £488 / night

                                                              Distance approx 19.5 miles from Winter Harbor

                                                                24

                                                                Surry holiday home rental

                                                                DownEast and Acadia Maine / Surry

                                                                3 8 7 nights min

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

                                                                from £233 / night

                                                                £1,626 - £2,013 / week

                                                                Enquire View

                                                                from £233 / night

                                                                Distance approx 14.33 miles from Winter Harbor

                                                                  30

                                                                  Trenton ski cottage to rent.

                                                                  DownEast and Acadia Maine / Trenton

                                                                  2 6 min stay varies

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

                                                                  from £133 / night

                                                                  £931 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 19 minutes

                                                                  from £133 / night

                                                                  Distance approx 1.75 miles from Winter Harbor Show on Map

                                                                  (1) Average 

                                                                    24

                                                                    Holiday cottage in South Gouldsboro

                                                                    DownEast and Acadia Maine / South Gouldsboro

                                                                    4 8 4 nights min

                                                                    • 4 bedrooms
                                                                    • sleeps 8
                                                                    • 4 nights min
                                                                    • Child friendly
                                                                    • Pet friendly

                                                                    from £191 / night

                                                                    £1,335 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 36 minutes

                                                                    from £191 / night

                                                                    Distance approx 12.37 miles from Winter Harbor

                                                                      13

                                                                      Holiday home rental

                                                                      Mount Desert Island / Mount Desert

                                                                      2 5 7 nights min

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

                                                                      from £228 / night

                                                                      £1,596 / week

                                                                      Book View

                                                                      from £228 / night

                                                                      Distance approx 2.96 miles from Winter Harbor

                                                                        4

                                                                        Birch Harbor holiday boathouse rental

                                                                        Gouldsboro / Birch Harbor

                                                                        2 4 1 night min

                                                                        • 2 bedrooms
                                                                        • sleeps 4
                                                                        • 1 night min
                                                                        • Pet friendly

                                                                        from £798 / night

                                                                        £5,319 / week

                                                                        Book View

                                                                        from £798 / night

                                                                        Distance approx 17.61 miles from Winter Harbor

                                                                        (24) Excellent 

                                                                          9

                                                                          Cottage rental in Acadia National Park

                                                                          Mount Desert Island / Acadia National Park

                                                                          1 2 7 nights min

                                                                          • 1 bedroom
                                                                          • sleeps 2
                                                                          • 7 nights min
                                                                          • Private garden

                                                                          from £144 / night

                                                                          £1,007 - £1,373 / week

                                                                          Book View

                                                                          from £144 / night

                                                                          Distance approx 17.64 miles from Winter Harbor

                                                                            36

                                                                            Holiday cottage in Tremont

                                                                            Mount Desert Island / Tremont

                                                                            2 7 7 nights min

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

                                                                            from £197 / night

                                                                            £1,374 / week

                                                                            Book View

                                                                            from £197 / night

                                                                            Distance approx 14.21 miles from Winter Harbor

                                                                              27

                                                                              Holiday home in Southwest Harbor

                                                                              Mount Desert Island / Southwest Harbor

                                                                              4 8 min stay varies

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

                                                                              from £191 / night

                                                                              £1,335 / week

                                                                              Book View

                                                                              Responds fast!
                                                                              avg. 19 minutes

                                                                              from £191 / night

                                                                              Distance approx 10.92 miles from Winter Harbor

                                                                                4

                                                                                Hulls Cove holiday apartment rental

                                                                                Bar Harbor / Hulls Cove

                                                                                2 2 7 nights min

                                                                                • 2 bedrooms
                                                                                • sleeps 2
                                                                                • 7 nights min
                                                                                • Private garden

                                                                                from £108 / night

                                                                                £754 / week

                                                                                Book View

                                                                                from £108 / night

                                                                                Distance approx 14.9 miles from Winter Harbor

                                                                                  4

                                                                                  Holiday home in Southwest Harbor

                                                                                  Mount Desert Island / Southwest Harbor

                                                                                  1 2 7 nights min

                                                                                  • 1 bedroom
                                                                                  • sleeps 2
                                                                                  • 7 nights min
                                                                                  • Nearest beach 2 km

                                                                                  from £156 / night

                                                                                  £1,086 / week

                                                                                  Book View

                                                                                  from £156 / night

                                                                                  Also consider