Guest houses in Windermere – Holiday Lettings - Holiday Rentals Windermere

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

77 Holiday homes

(8) Excellent 

    19

    Holiday guest house with golf nearby in Windermere

    Muskoka Lakes / Windermere

    2 4 3 nights min

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

    from £162 / night

    £969 / week

    Book View

    from £162 / night

    Great rentals within 20 miles that match your search

    Distance approx 6.28 miles from Windermere

    (8) Excellent 

      22

      Muskoka Lakes holiday cottage rental

      Muskoka District / Muskoka Lakes

      6 12 7 nights min

      • 6 bedrooms
      • sleeps 12
      • 7 nights min
      • Beach / lakeside relaxation
      • Child friendly
      • Air conditioning

      from £406 / night

      £2,840 - £5,745 / week

      Book View

      Responds fast!
      avg. 3 hours 12 minutes

      from £406 / night

      Distance approx 15.31 miles from Windermere

        17

        Bracebridge holiday tented camp rental

        Muskoka District / Bracebridge

        1 2 2 nights min

        • 1 bedroom
        • sleeps 2
        • 2 nights min

        from £251 / night

        £1,758 / week

        Book View

        from £251 / night

        Distance approx 14.12 miles from Windermere

        (1) Excellent 

          20

          Holiday cottage in Port Sydney

          Huntsville / Port Sydney

          3 6 min stay varies

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

          from £194 / night

          £1,017 / week

          Book View

          from £194 / night

          Distance approx 15.45 miles from Windermere

            8

            Holiday cottage letting

            Muskoka District / Mactier

            2 4 7 nights min

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

            from £121 / night

            £650 / week

            Book View

            from £121 / night

            Distance approx 17.66 miles from Windermere

            (4) Excellent 

              30

              Holiday cottage in Huntsville

              Muskoka District / Huntsville

              3 9 7 nights min

              • 3 bedrooms
              • sleeps 9
              • 7 nights min
              • Beach / lakeside relaxation
              • Child friendly

              from £176 / night

              £1,227 / week

              Book View

              from £176 / night

              Distance approx 3.78 miles from Windermere

                48

                Holiday cottage in Port Carling

                Muskoka Lakes / Port Carling

                6 14 min stay varies

                • 6 bedrooms
                • sleeps 14
                • min stay varies
                • Beach / lakeside relaxation
                • Child friendly
                • Air conditioning

                from £665 / night

                £4,650 - £6,642 / week

                Book View

                Responds fast!
                avg. 4 minutes

                from £665 / night

                Distance approx 14.11 miles from Windermere

                  27

                  Holiday cottage accommodation

                  Huntsville / Port Sydney

                  5 10 min stay varies

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

                  from £310 / night

                  £1,608 / week

                  Book View

                  from £310 / night

                  Distance approx 13.18 miles from Windermere

                  (1) Excellent 

                    16

                    Bracebridge holiday cottage rental

                    Muskoka District / Bracebridge

                    4 8 7 nights min

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

                    from £304 / night

                    £2,124 / week

                    Book View

                    Responds fast!
                    avg. 3 hours 59 minutes

                    from £304 / night

                    Distance approx 19.27 miles from Windermere

                    (1) Excellent 

                      28

                      Holiday cottage in Port Severn

                      Muskoka District / Port Severn

                      3 6 min stay varies

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

                      from £210 / night

                      £1,404 - £2,000 / week

                      Book View

                      from £210 / night

                      Distance approx 16.59 miles from Windermere

                        10

                        Gravenhurst holiday cottage rental

                        Muskoka District / Gravenhurst

                        4 10 2 nights min

                        • 4 bedrooms
                        • sleeps 10
                        • 2 nights min
                        • Child friendly
                        • Pet friendly
                        • Private garden

                        from £355 / night

                        £2,481 / week

                        Book View

                        from £355 / night

                        Distance approx 11.72 miles from Windermere

                        (1) Excellent 

                          30

                          Bracebridge holiday home rental

                          Muskoka District / Bracebridge

                          3 8 1 night min

                          • 3 bedrooms
                          • sleeps 8
                          • 1 night min
                          • Nearest beach 0.05 km
                          • Child friendly
                          • Pet friendly

                          from £163 / night

                          £1,104 / week

                          Book View

                          from £163 / night

                          Distance approx 14.18 miles from Windermere

                          (1) Excellent 

                            23

                            Port Sydney holiday cottage rental

                            Huntsville / Port Sydney

                            2 4 min stay varies

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

                            from £146 / night

                            £872 / week

                            Book View

                            from £146 / night

                            Distance approx 12.17 miles from Windermere

                            (3) Very Good 

                              13

                              Holiday cottage in Muskoka Lakes

                              Muskoka District / Muskoka Lakes

                              4 12 7 nights min

                              • 4 bedrooms
                              • sleeps 12
                              • 7 nights min
                              • Nearest beach 0.1 km
                              • Child friendly
                              • Private garden

                              from £484 / night

                              £3,228 / week

                              Book View

                              from £484 / night

                              Distance approx 19.53 miles from Windermere

                              (3) Excellent 

                                25

                                Cottage rental in Huntsville

                                Muskoka District / Huntsville

                                4 10 1 night min

                                • 4 bedrooms
                                • sleeps 10
                                • 1 night min
                                • Beach / lakeside relaxation
                                • Nearest beach 0.1 km
                                • Child friendly

                                from £194 / night

                                £1,291 / week

                                Book View

                                Responds fast!
                                avg. 3 hours 15 minutes

                                from £194 / night

                                Distance approx 8.2 miles from Windermere

                                (1) Very Good 

                                  18

                                  Holiday cottage in Mactier

                                  Muskoka District / Mactier

                                  7 15 7 nights min

                                  • 7 bedrooms
                                  • sleeps 15
                                  • 7 nights min
                                  • Child friendly
                                  • Pet friendly

                                  from £259 / night

                                  £1,808 / week

                                  Book View

                                  Responds fast!
                                  avg. 3 hours 7 minutes

                                  from £259 / night

                                  Distance approx 2.99 miles from Windermere Show on Map

                                    46

                                    Holiday cottage in Port Carling

                                    Muskoka Lakes / Port Carling

                                    3 6 min stay varies

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

                                    from £204 / night

                                    £1,424 - £2,372 / week

                                    Book View

                                    Responds fast!
                                    avg. 4 minutes

                                    from £204 / night

                                    Distance approx 19.37 miles from Windermere

                                      19

                                      Gravenhurst holiday cottage rental

                                      Muskoka District / Gravenhurst

                                      4 8 min stay varies

                                      • 4 bedrooms
                                      • sleeps 8
                                      • min stay varies
                                      • Beach / lakeside relaxation
                                      • Child friendly
                                      • Ask about pets

                                      from £195 / night

                                      £1,304 - £1,672 / week

                                      Book View

                                      Responds fast!
                                      avg. 3 hours 42 minutes

                                      from £195 / night

                                      Distance approx 18.44 miles from Windermere

                                        17

                                        Gravenhurst holiday villa rental

                                        Muskoka District / Gravenhurst

                                        4 12 6 nights min

                                        • 4 bedrooms
                                        • sleeps 12
                                        • 6 nights min
                                        • Child friendly
                                        • Air conditioning
                                        • Pet friendly

                                        from £446 / night

                                        £3,118 / week

                                        Book View

                                        from £446 / night

                                        Distance approx 17.76 miles from Windermere

                                          9

                                          Holiday home in Muskoka Lakes

                                          Muskoka District / Muskoka Lakes

                                          3 8 7 nights min

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

                                          from £277 / night

                                          £1,934 / week

                                          Book View

                                          from £277 / night

                                          Distance approx 19.36 miles from Windermere

                                            15

                                            Holiday villa rental

                                            Muskoka District / Gravenhurst

                                            1 5 2 nights min

                                            • 1 bedroom
                                            • sleeps 5
                                            • 2 nights min
                                            • Swimming pool
                                            • Child friendly
                                            • Air conditioning

                                            from £162 / night

                                            £581 - £586 / week

                                            Book View

                                            Responds fast!
                                            avg. 37 minutes

                                            from £162 / night

                                            Distance approx 3.91 miles from Windermere

                                              10

                                              Minett holiday cottage rental

                                              Muskoka Lakes / Minett

                                              4 12 7 nights min

                                              • 4 bedrooms
                                              • sleeps 12
                                              • 7 nights min
                                              • Child friendly
                                              • Pet friendly

                                              from £870 / night

                                              £4,349 - £5,567 / week

                                              Book View

                                              from £870 / night

                                              Distance approx 8.2 miles from Windermere

                                                13

                                                Holiday home in Muskoka Lakes

                                                Muskoka District / Muskoka Lakes

                                                4 2 7 nights min

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

                                                from £166 / night

                                                £1,162 / week

                                                Book View

                                                Responds fast!
                                                avg. 3 hours 7 minutes

                                                from £166 / night

                                                Distance approx 17.53 miles from Windermere

                                                  44

                                                  Holiday cottage in Kawartha Lakes

                                                  Ontario / Kawartha Lakes

                                                  3 8 7 nights min

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

                                                  from £259 / night

                                                  £1,808 / week

                                                  Book View

                                                  from £259 / night

                                                  Distance approx 10.68 miles from Windermere

                                                    89

                                                    Holiday home in Minett

                                                    Muskoka Lakes / Minett

                                                    5 14 min stay varies

                                                    • 5 bedrooms
                                                    • sleeps 14
                                                    • min stay varies
                                                    • Beach / lakeside relaxation
                                                    • Child friendly
                                                    • Air conditioning

                                                    from £441 / night

                                                    £3,457 - £6,168 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 4 minutes

                                                    from £441 / night

                                                    Distance approx 10.83 miles from Windermere

                                                      38

                                                      Ski cottage to rent in Bala

                                                      Muskoka Lakes / Bala

                                                      4 8 min stay varies

                                                      • 4 bedrooms
                                                      • sleeps 8
                                                      • min stay varies
                                                      • Beach / lakeside relaxation
                                                      • Ski
                                                      • Child friendly

                                                      from £624 / night

                                                      £4,698 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 4 minutes

                                                      from £624 / night

                                                      Distance approx 16.76 miles from Windermere

                                                      (1) Very Good 

                                                        25

                                                        Huntsville holiday cottage rental

                                                        Muskoka District / Huntsville

                                                        3 8 7 nights min

                                                        • 3 bedrooms
                                                        • sleeps 8
                                                        • 7 nights min
                                                        • Child friendly
                                                        • Ask about pets

                                                        from £194 / night

                                                        £1,356 / week

                                                        Book View

                                                        from £194 / night

                                                        Distance approx 14.47 miles from Windermere

                                                        (2) Excellent 

                                                          25

                                                          Holiday cottage in Huntsville

                                                          Muskoka District / Huntsville

                                                          4 12 min stay varies

                                                          • 4 bedrooms
                                                          • sleeps 12
                                                          • min stay varies
                                                          • Beach / lakeside relaxation
                                                          • Child friendly

                                                          from £163 / night

                                                          £1,137 - £1,559 / week

                                                          Book View

                                                          from £163 / night

                                                          Distance approx 14.18 miles from Windermere

                                                            24

                                                            Port Sydney holiday cottage accommodation

                                                            Huntsville / Port Sydney

                                                            3 6 min stay varies

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

                                                            from £194 / night

                                                            £994 / week

                                                            Book View

                                                            from £194 / night

                                                            Distance approx 19.28 miles from Windermere

                                                              12

                                                              Holiday cottage in Big Chute

                                                              Muskoka District / Big Chute

                                                              4 8 7 nights min

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

                                                              from £185 / night

                                                              £1,291 / week

                                                              Book View

                                                              from £185 / night

                                                              Distance approx 8.62 miles from Windermere

                                                                15

                                                                Cottage letting in Mactier with golf nearby

                                                                Muskoka District / Mactier

                                                                4 8 5 nights min

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

                                                                from £646 / night

                                                                £4,519 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 3 hours 32 minutes

                                                                from £646 / night

                                                                Distance approx 7.13 miles from Windermere

                                                                  100

                                                                  Holiday home in Muskoka Lakes

                                                                  Muskoka District / Muskoka Lakes

                                                                  14 20 4 nights min

                                                                  • 14 bedrooms
                                                                  • sleeps 20
                                                                  • 4 nights min
                                                                  • Beach / lakeside relaxation
                                                                  • Child friendly
                                                                  • Pet friendly

                                                                  from £3,389 / night

                                                                  £23,721 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 4 minutes

                                                                  from £3,389 / night

                                                                  Distance approx 12.08 miles from Windermere

                                                                    35

                                                                    Holiday cottage in Gravenhurst

                                                                    Muskoka District / Gravenhurst

                                                                    4 10 min stay varies

                                                                    • 4 bedrooms
                                                                    • sleeps 10
                                                                    • min stay varies
                                                                    • Beach / lakeside relaxation
                                                                    • Child friendly
                                                                    • Air conditioning

                                                                    from £534 / night

                                                                    £4,203 - £7,253 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 4 minutes

                                                                    from £534 / night

                                                                    Distance approx 9.91 miles from Windermere

                                                                      50

                                                                      Bala ski home to rent.

                                                                      Muskoka Lakes / Bala

                                                                      7 12 min stay varies

                                                                      • 7 bedrooms
                                                                      • sleeps 12
                                                                      • min stay varies
                                                                      • Beach / lakeside relaxation
                                                                      • Ski
                                                                      • Child friendly

                                                                      from £1,211 / night

                                                                      £8,474 - £9,152 / week

                                                                      Book View

                                                                      Responds fast!
                                                                      avg. 4 minutes

                                                                      from £1,211 / night

                                                                      Distance approx 8.6 miles from Windermere

                                                                        24

                                                                        Cottage rental in Muskoka Lakes

                                                                        Muskoka District / Muskoka Lakes

                                                                        4 10 min stay varies

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

                                                                        from £275 / night

                                                                        £1,921 / week

                                                                        Book View

                                                                        from £275 / night

                                                                        Distance approx 12.76 miles from Windermere

                                                                          37

                                                                          Holiday home in Seguin

                                                                          Northeastern Ontario / Seguin

                                                                          5 11 min stay varies

                                                                          • 5 bedrooms
                                                                          • sleeps 11
                                                                          • min stay varies
                                                                          • Beach / lakeside relaxation
                                                                          • Child friendly
                                                                          • Air conditioning

                                                                          from £462 / night

                                                                          £3,228 - £6,461 / week

                                                                          Book View

                                                                          Responds fast!
                                                                          avg. 4 minutes

                                                                          from £462 / night

                                                                          Distance approx 17.94 miles from Windermere

                                                                            15

                                                                            Holiday cottage in Gravenhurst

                                                                            Muskoka District / Gravenhurst

                                                                            4 8 3 nights min

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

                                                                            from £323 / night

                                                                            £2,260 / week

                                                                            Book View

                                                                            from £323 / night

                                                                            Distance approx 15.45 miles from Windermere

                                                                            (80) Excellent 

                                                                              73

                                                                              Gravenhurst holiday cottage rental

                                                                              Muskoka District / Gravenhurst

                                                                              5 10 min stay varies

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

                                                                              from £384 / night

                                                                              £4,422 / week

                                                                              Book View

                                                                              Responds fast!
                                                                              avg. 51 minutes

                                                                              from £384 / night

                                                                              Distance approx 5.59 miles from Windermere

                                                                                8

                                                                                Holiday cottage in Port Loring

                                                                                Northeastern Ontario / Port Loring

                                                                                2 4 7 nights min

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

                                                                                from £93 / night

                                                                                £646 / week

                                                                                Book View

                                                                                from £93 / night

                                                                                Distance approx 4.34 miles from Windermere

                                                                                  81

                                                                                  Holiday home in Port Carling

                                                                                  Muskoka Lakes / Port Carling

                                                                                  7 14 60 nights min

                                                                                  • 7 bedrooms
                                                                                  • sleeps 14
                                                                                  • 60 nights min
                                                                                  • Child friendly
                                                                                  • Air conditioning
                                                                                  • Pet friendly

                                                                                  from £904 / night

                                                                                  £6,794 - £9,376 / week

                                                                                  Book View

                                                                                  Responds fast!
                                                                                  avg. 4 minutes

                                                                                  from £904 / night

                                                                                  Also consider