Estates in Windham and Houses - Holiday Lettings - Holiday Rentals Windham

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

87 Holiday homes

    102

    Holiday home letting

    Maine / Windham

    3 9 min stay varies

    • 3 bedrooms
    • sleeps 9
    • min stay varies
    • Child friendly
    • Car not necessary
    • Air conditioning

    from £115 / night

    £801 / week

    Book View

    Responds fast!
    avg. 3 hours 4 minutes

    from £115 / night

      33

      Home rental in Windham

      Maine / Windham

      5 8 min stay varies

      • 5 bedrooms
      • sleeps 8
      • min stay varies
      • Child friendly
      • Car not necessary
      • Air conditioning

      from £236 / night

      £1,651 / week

      Book View

      Responds fast!
      avg. 1 hour 18 minutes

      from £236 / night

        15

        Holiday home in Windham

        Maine / Windham

        3 8 7 nights min

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

        from £236 / night

        £1,647 / week

        Book View

        from £236 / night

          17

          Home rental in Windham

          Maine / Windham

          1 6 2 nights min

          • 1 bedroom
          • sleeps 6
          • 2 nights min
          • Child friendly
          • Car not necessary
          • Air conditioning

          from £135 / night

          £941 / week

          Book View

          Responds fast!
          avg. 3 hours 4 minutes

          from £135 / night

            0

            Holiday home in Windham

            Maine / Windham

            3 6 min stay varies

            • 3 bedrooms
            • sleeps 6
            • min stay varies
            • Child friendly
            • Car not necessary
            • Air conditioning

            from £236 / night

            £1,651 / week

            Book View

            Responds fast!
            avg. 3 hours 4 minutes

            from £236 / night

              5

              Holiday cottage in Windham

              Maine / Windham

              3 6 7 nights min

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

              from £217 / night

              £1,301 / week

              Book View

              Responds fast!
              avg. 2 hours 32 minutes

              from £217 / night

                13

                Holiday cottage in Windham

                Maine / Windham

                2 6 min stay varies

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

                from £87 / night

                £607 / week

                Book View

                from £87 / night

                Great rentals within 20 miles that match your search

                Distance approx 15.99 miles from Windham

                (2) Excellent 

                  13

                  Cottage letting in Poland

                  Maine / Poland

                  2 7 min stay varies

                  • 2 bedrooms
                  • sleeps 7
                  • min stay varies
                  • Nearest beach 0 km
                  • Child friendly
                  • Pet friendly

                  from £86 / night

                  £737 - £1,083 / week

                  Book View

                  from £86 / night

                  Distance approx 9.76 miles from Windham

                  (11) Very Good 

                    26

                    Holiday cottage letting

                    Maine / Sebago

                    4 8 min stay varies

                    • 4 bedrooms
                    • sleeps 8
                    • min stay varies
                    • Beach / lakeside relaxation
                    • Nearest beach 2 km
                    • Child friendly

                    from £179 / night

                    £1,218 - £1,653 / week

                    Book View

                    Responds fast!
                    avg. 1 hour 34 minutes

                    from £179 / night

                    Distance approx 9.86 miles from Windham

                    (1) Excellent 

                      14

                      Holiday cottage rental

                      Maine / Sebago

                      4 8 7 nights min

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

                      from £248 / night

                      £1,387 - £1,821 / week

                      Book View

                      Responds fast!
                      avg. 3 hours 39 minutes

                      from £248 / night

                      Distance approx 13.45 miles from Windham

                        43

                        Holiday home in Naples

                        Maine / Naples

                        2 6 7 nights min

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

                        from £223 / night

                        £1,561 / week

                        Book View

                        from £223 / night

                        Distance approx 17.22 miles from Windham

                          15

                          Holiday home in Scarborough

                          Maine / Scarborough

                          4 10 7 nights min

                          • 4 bedrooms
                          • sleeps 10
                          • 7 nights min
                          • Beach / lakeside relaxation
                          • Nearest beach 2 km
                          • Ask owner if suitable for children

                          from £867 / night

                          £6,068 / week

                          Book View

                          from £867 / night

                          Distance approx 13.54 miles from Windham

                            24

                            Portland holiday apartment rental

                            Maine / Portland

                            5 10 3 nights min

                            • 5 bedrooms
                            • sleeps 10
                            • 3 nights min
                            • Child friendly
                            • Air conditioning
                            • Pet friendly

                            from £217 / night

                            £1,517 / week

                            Book View

                            from £217 / night

                            Distance approx 18 miles from Windham

                              15

                              Cape Elizabeth holiday home rental

                              Maine / Cape Elizabeth

                              5 10 min stay varies

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

                              from £779 / night

                              £3,023 - £6,850 / week

                              Book View

                              Responds fast!
                              avg. 2 hours 40 minutes

                              from £779 / night

                              Distance approx 17.74 miles from Windham

                                25

                                Holiday cottage in Denmark

                                Maine / Denmark

                                5 10 min stay varies

                                • 5 bedrooms
                                • sleeps 10
                                • min stay varies
                                • Child friendly

                                from £130 / night

                                £911 / week

                                Book View

                                Responds fast!
                                avg. 58 minutes

                                from £130 / night

                                Distance approx 19.76 miles from Windham

                                (6) Excellent 

                                Certificate of Excellence

                                  49

                                  Holiday cottage in Denmark

                                  Maine / Denmark

                                  1 4 min stay varies

                                  • 1 bedroom
                                  • sleeps 4
                                  • min stay varies
                                  • Nearest beach 11 km
                                  • Child friendly
                                  • Air conditioning

                                  Certificate of Excellence

                                  from £65 / night

                                  £390 - £633 / week

                                  Book View

                                  Responds fast!
                                  avg. 2 hours 36 minutes

                                  from £65 / night

                                  Distance approx 17.25 miles from Windham

                                    9

                                    Holiday apartment in South Portland

                                    Maine / South Portland

                                    2 4 2 nights min

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

                                    from £109 / night

                                    £564 / week

                                    Book View

                                    from £109 / night

                                    Distance approx 17.29 miles from Windham

                                    (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 £256 / night

                                      £1,626 - £4,295 / week

                                      Book View

                                      Responds fast!
                                      avg. 2 hours 40 minutes

                                      from £256 / night

                                      Distance approx 11.69 miles from Windham

                                        24

                                        Holiday log cabin in Naples

                                        Maine / Naples

                                        3 8 min stay varies

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

                                        from £117 / night

                                        £820 / week

                                        Book View

                                        Responds fast!
                                        avg. 58 minutes

                                        from £117 / night

                                        Distance approx 17.17 miles from Windham

                                        (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 £366 / night

                                          £2,557 / week

                                          Book View

                                          from £366 / night

                                          Distance approx 16.53 miles from Windham

                                            25

                                            South Freeport holiday cottage rental

                                            Maine / South Freeport

                                            1 4 min stay varies

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

                                            from £200 / night

                                            £1,396 / week

                                            Book View

                                            Responds fast!
                                            avg. 8 minutes

                                            from £200 / night

                                            Distance approx 13.13 miles from Windham

                                              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

                                              £631 / week

                                              Book View

                                              Responds fast!
                                              avg. 3 hours 37 minutes

                                              from £113 / night

                                              Distance approx 17.41 miles from Windham

                                                6

                                                Holiday cottage in Bridgton

                                                Maine / Bridgton

                                                2 6 2 nights min

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

                                                from £130 / night

                                                £954 / week

                                                Book View

                                                from £130 / night

                                                Distance approx 16.53 miles from Windham

                                                  24

                                                  South Freeport holiday cottage rental

                                                  Maine / South Freeport

                                                  2 6 min stay varies

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

                                                  from £217 / night

                                                  £1,517 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 8 minutes

                                                  from £217 / night

                                                  Distance approx 13.66 miles from Windham

                                                    11

                                                    Falmouth holiday cottage rental

                                                    Maine / Falmouth

                                                    3 5 min stay varies

                                                    • 3 bedrooms
                                                    • sleeps 5
                                                    • min stay varies
                                                    • Nearest beach 0.01 km
                                                    • Child friendly
                                                    • Pet friendly

                                                    from £174 / night

                                                    £1,561 / week

                                                    Book View

                                                    from £174 / night

                                                    Distance approx 17.27 miles from Windham

                                                      63

                                                      Holiday home with golf nearby in South Portland

                                                      Maine / South Portland

                                                      4 13 min stay varies

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

                                                      from £516 / night

                                                      £3,013 - £6,480 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 2 hours 40 minutes

                                                      from £516 / night

                                                      Distance approx 11.69 miles from Windham

                                                        7

                                                        Holiday home in Naples

                                                        Maine / Naples

                                                        2 8 7 nights min

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

                                                        from £174 / night

                                                        £1,214 / week

                                                        Book View

                                                        from £174 / night

                                                        Distance approx 5.14 miles from Windham

                                                          44

                                                          Holiday home in Raymond

                                                          Maine / Raymond

                                                          4 16 min stay varies

                                                          • 4 bedrooms
                                                          • sleeps 16
                                                          • min stay varies
                                                          • Child friendly
                                                          • Air conditioning
                                                          • Private garden

                                                          from £603 / night

                                                          £6,038 / week

                                                          Book View

                                                          from £603 / night

                                                          Distance approx 7.68 miles from Windham

                                                            21

                                                            Holiday home accommodation

                                                            Mount Desert Island / Mount Desert

                                                            3 8 7 nights min

                                                            • 3 bedrooms
                                                            • sleeps 8
                                                            • 7 nights min
                                                            • Swimming pool
                                                            • Child friendly
                                                            • Air conditioning

                                                            from £249 / night

                                                            £1,742 / week

                                                            Book View

                                                            from £249 / night

                                                            Distance approx 16.8 miles from Windham

                                                              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 £429 / night

                                                              £2,579 - £5,613 / week

                                                              Book View

                                                              Responds fast!
                                                              avg. 2 hours 40 minutes

                                                              from £429 / night

                                                              Distance approx 9.97 miles from Windham

                                                                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 £52 / night

                                                                £358 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 8 minutes

                                                                from £52 / night

                                                                Distance approx 10.62 miles from Windham

                                                                  24

                                                                  Ski cottage to rent in Naples

                                                                  Maine / Naples

                                                                  2 4 2 nights min

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

                                                                  from £127 / night

                                                                  £884 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 21 minutes

                                                                  from £127 / night

                                                                  Distance approx 12.21 miles from Windham

                                                                    37

                                                                    Ski home to rent in Naples

                                                                    Maine / Naples

                                                                    4 8 min stay varies

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

                                                                    from £559 / night

                                                                    £3,914 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 58 minutes

                                                                    from £559 / night

                                                                    Distance approx 15.21 miles from Windham

                                                                      40

                                                                      Holiday apartment in Portland

                                                                      Maine / Portland

                                                                      3 9 min stay varies

                                                                      • 3 bedrooms
                                                                      • sleeps 9
                                                                      • min stay varies
                                                                      • Nearest beach 0.4 km
                                                                      • Child friendly
                                                                      • Air conditioning

                                                                      from £308 / night

                                                                      £1,994 - £2,965 / week

                                                                      Book View

                                                                      Responds fast!
                                                                      avg. 2 hours 28 minutes

                                                                      from £308 / night

                                                                      Distance approx 10.92 miles from Windham

                                                                        28

                                                                        Holiday home in Naples

                                                                        Maine / Naples

                                                                        3 8 min stay varies

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

                                                                        from £165 / night

                                                                        £1,153 / week

                                                                        Book View

                                                                        Responds fast!
                                                                        avg. 58 minutes

                                                                        from £165 / night

                                                                        Distance approx 11.2 miles from Windham

                                                                          18

                                                                          Holiday home in Westbrook

                                                                          Maine / Westbrook

                                                                          5 20 7 nights min

                                                                          • 5 bedrooms
                                                                          • sleeps 20
                                                                          • 7 nights min
                                                                          • Nearest beach 14 km
                                                                          • Child friendly
                                                                          • Air conditioning

                                                                          from £824 / night

                                                                          £5,765 / week

                                                                          Book View

                                                                          from £824 / night

                                                                          Distance approx 15.07 miles from Windham

                                                                            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

                                                                            £607 - £2,427 / week

                                                                            Book View

                                                                            from £87 / night

                                                                            Distance approx 15.07 miles from Windham

                                                                              5

                                                                              Portland holiday apartment rental

                                                                              Maine / Portland

                                                                              3 6 min stay varies

                                                                              • 3 bedrooms
                                                                              • sleeps 6
                                                                              • min stay varies
                                                                              • Nearest beach 1 km
                                                                              • Child friendly
                                                                              • Car not necessary

                                                                              from £217 / night

                                                                              £1,214 - £3,944 / week

                                                                              Book View

                                                                              from £217 / night

                                                                              Distance approx 16.71 miles from Windham

                                                                                14

                                                                                Holiday apartment in Freeport

                                                                                Maine / Freeport

                                                                                2 5 2 nights min

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

                                                                                from £109 / night

                                                                                £867 - £989 / week

                                                                                Book View

                                                                                from £109 / night

                                                                                Distance approx 15.43 miles from Windham

                                                                                (1) Excellent 

                                                                                  6

                                                                                  Home letting in Portland

                                                                                  Maine / Portland

                                                                                  1 2 3 nights min

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

                                                                                  from £154 / night

                                                                                  £1,074 / week

                                                                                  Book View

                                                                                  from £154 / night

                                                                                  Also consider