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58 Houses

(8) Excellent 

    19

    The Roost Cottage, Windermere, Muskoka, Ontario

    Muskoka Lakes / Windermere

    Windermere guest house

    2 4 3 nights min

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

    Price per night from

    $215

    Price per night from

    $215

    Great rentals within 20 miles that match your search

    Distance approx 14.12 km from Windermere

    (1) Excellent 

      20

      White Cottage - Clyffe House Cottage Resort

      Huntsville / Port Sydney

      Port Sydney cottage

      3 6 7 nights min

      • 3 bedrooms
      • sleeps 6
      • 7 nights min
      • Child Friendly

      Price per night from

      $189

      Price per night from

      $189

      Distance approx 4.94 km from Windermere

        35

        Muskoka Birch On Lake Rosseau

        Muskoka Lakes / Minett

        Minett cottage

        5 8 7 nights min

        • 5 bedrooms
        • sleeps 8
        • 7 nights min
        • Beach / lakeside relaxation
        • Nearest beach 0.01 mi
        • Child Friendly

        Price per night from

        $344

        Price per night from

        $344

        Distance approx 5.51 km from Windermere Show on Map

          35

          Cherry Island Luxury Private Island

          Northeastern Ontario / Rosseau

          Rosseau cottage

          6 18 min stay varies

          • 6 bedrooms
          • sleeps 18
          • min stay varies
          • Beach / lakeside relaxation
          • Nearest beach 0.2 mi
          • Child Friendly

          Price per night from

          $1,718

          Price per night from

          $1,718

          Distance approx 18.56 km from Windermere

          (4) Excellent 

            28

            3 Bedroom Cottage on Beautiful Horseshoe Lake

            Northeastern Ontario / Parry Sound

            Parry Sound cottage

            3 6 7 nights min

            • 3 bedrooms
            • sleeps 6
            • 7 nights min
            • Beach / lakeside relaxation
            • Suitable for children age 5+
            • Ask about pets

            Price per night from

            $184

            Responds fast!
            avg. 3 hours 13 minutes

            Price per night from

            $184

            Distance approx 13.18 km from Windermere

            (1) Excellent 

              16

              Lake Muskoka Getaway

              Muskoka District / Bracebridge

              Bracebridge cottage

              4 8 7 nights min

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

              Price per night from

              $401

              Price per night from

              $401

              Distance approx 19.27 km from Windermere

              (1) Excellent 

                28

                Muskoka Rustic Beauty - Cottage Six Mile Lake

                Muskoka District / Port Severn

                Port Severn cottage

                3 6 min stay varies

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

                Price per night from

                $280

                Price per night from

                $280

                Distance approx 14.11 km from Windermere

                  27

                  Dining Room Cottage - Clyffe House Cottage Resort

                  Huntsville / Port Sydney

                  Port Sydney cottage

                  5 10 7 nights min

                  • 5 bedrooms
                  • sleeps 10
                  • 7 nights min
                  • Child Friendly

                  Price per night from

                  $299

                  Price per night from

                  $299

                  Distance approx 14.05 km from Windermere

                  (3) Very Good 

                    29

                    The Main Lodge Cottage - Clyffe House Cottage Resort

                    Huntsville / Port Sydney

                    Port Sydney cottage

                    5 12 2 nights min

                    • 5 bedrooms
                    • sleeps 12
                    • 2 nights min
                    • Child Friendly

                    Price per night from

                    $214

                    Price per night from

                    $214

                    Distance approx 17.66 km from Windermere

                    (4) Excellent 

                      30

                      Beautiful Quiet Cottage on Fox Lake in Huntsville, Ontario

                      Muskoka District / Huntsville

                      Huntsville cottage

                      3 9 7 nights min

                      • 3 bedrooms
                      • sleeps 9
                      • 7 nights min
                      • Beach / lakeside relaxation
                      • Child Friendly
                      “Peaceful, Beautiful Cottage” Hello, I stayed at this cottage this past weekend with a couple of my girlfriends. We where looking for a quiet remote location to relax, enjoy the sun, and bonfire in the afternoon. Upon arrival to the cottage we where g
                      …see more

                      Price per night from

                      $233

                      Price per night from

                      $233

                      Distance approx 11.72 km from Windermere

                      (1) Excellent 

                        30

                        Cozy Lake Muskoka Cottage on Bowyers Beach Rd

                        Muskoka District / Bracebridge

                        Bracebridge house

                        3 8 1 night min

                        • 3 bedrooms
                        • sleeps 8
                        • 1 night min
                        • Nearest beach 0.05 mi
                        • Child Friendly
                        • Pet Friendly

                        Price per night from

                        $215

                        Price per night from

                        $215

                        Distance approx 16.59 km from Windermere

                          10

                          Sandy Pines Cottage on Muskoka Beach

                          Muskoka District / Gravenhurst

                          Gravenhurst cottage

                          4 10 2 nights min

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

                          Price per night from

                          $472

                          Price per night from

                          $472

                          Distance approx 10.82 km from Windermere

                          (13) Excellent 

                            31

                            Lake Muskoka - Executive Post & Beam Architecture, 2800 sf -Four Season-Island

                            Muskoka District / Muskoka Lakes

                            Muskoka Lakes cottage

                            4 10 min stay varies

                            • 4 bedrooms
                            • sleeps 10
                            • min stay varies
                            • Beach / lakeside relaxation
                            • Child Friendly
                            • Car not necessary

                            Price per night from

                            $580

                            Responds fast!
                            avg. 3 hours 56 minutes

                            Price per night from

                            $580

                            Distance approx 19.53 km from Windermere

                            (3) Excellent 

                              25

                              Awesome Buck Lake Cottage - ATV-Sled-Relax-FUN!

                              Muskoka District / Huntsville

                              Huntsville cottage

                              4 10 1 night min

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

                              Price per night from

                              $258

                              Responds fast!
                              avg. 3 hours 3 minutes

                              Price per night from

                              $258

                              Distance approx 8.2 km from Windermere

                              (1) Very Good 

                                18

                                Muskoka, bass lake

                                Muskoka District / Mactier

                                Mactier cottage

                                7 15 7 nights min

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

                                Price per night from

                                $344

                                Price per night from

                                $344

                                Distance approx 19.53 km from Windermere

                                (4) Excellent 

                                  32

                                  'Mellow Yellow' - 5 Bedroom Luxury Muskoka Cottage

                                  Muskoka District / Gravenhurst

                                  Gravenhurst cottage

                                  5 12 3 nights min

                                  • 5 bedrooms
                                  • sleeps 12
                                  • 3 nights min
                                  • Beach / lakeside relaxation
                                  • Child Friendly
                                  • Ask about pets

                                  Price per night from

                                  $458

                                  Responds fast!
                                  avg. 3 hours 47 minutes

                                  Price per night from

                                  $458

                                  Distance approx 14.18 km from Windermere

                                  (1) Excellent 

                                    23

                                    Ice Palace - Clyffe House Cottage Resort

                                    Huntsville / Port Sydney

                                    Port Sydney cottage

                                    2 4 7 nights min

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

                                    Price per night from

                                    $159

                                    Price per night from

                                    $159

                                    Distance approx 19.37 km from Windermere

                                      19

                                      Private 4 Bedroom Muskoka Cottage

                                      Muskoka District / Gravenhurst

                                      Gravenhurst cottage

                                      4 8 min stay varies

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

                                      Price per night from

                                      $260

                                      Responds fast!
                                      avg. 3 hours 36 minutes

                                      Price per night from

                                      $260

                                      Distance approx 13.97 km from Windermere

                                      (1) Excellent 

                                        9

                                        Muskoka Lakes, Bass lake, Port Carling and Bala

                                        Ontario / Muskoka District

                                        Muskoka District cottage

                                        5 12 7 nights min

                                        • 5 bedrooms
                                        • sleeps 12
                                        • 7 nights min
                                        • Beach / lakeside relaxation
                                        • Child Friendly
                                        • Car not necessary

                                        Price per night from

                                        $343

                                        Responds fast!
                                        avg. 42 minutes

                                        Price per night from

                                        $343

                                        Distance approx 8.2 km from Windermere

                                          13

                                          Muskoka, bass lake Cottage No. 2

                                          Muskoka District / Muskoka Lakes

                                          Muskoka Lakes house

                                          4 2 7 nights min

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

                                          Price per night from

                                          $221

                                          Price per night from

                                          $221

                                          Distance approx 14.18 km from Windermere

                                          (1) Excellent 

                                            25

                                            Dance Hall (Upper) - Clyffe House Cottage Resort

                                            Huntsville / Port Sydney

                                            Port Sydney cottage

                                            3 6 7 nights min

                                            • 3 bedrooms
                                            • sleeps 6
                                            • 7 nights min
                                            • Nearest beach 0 mi
                                            • Child Friendly

                                            Price per night from

                                            $182

                                            Price per night from

                                            $182

                                            Distance approx 18.44 km from Windermere

                                              17

                                              BedRock Mansion Retreat

                                              Muskoka District / Gravenhurst

                                              Gravenhurst villa

                                              4 12 6 nights min

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

                                              Price per night from

                                              $593

                                              Price per night from

                                              $593

                                              Distance approx 18.04 km from Windermere

                                              (2) Excellent 

                                                36

                                                Lake Muskoka Cottage Rental

                                                Muskoka District / Muskoka Lakes

                                                Muskoka Lakes cottage

                                                5 11 7 nights min

                                                • 5 bedrooms
                                                • sleeps 11
                                                • 7 nights min
                                                • Beach / lakeside relaxation
                                                • Child Friendly
                                                • Car not necessary

                                                Price per night from

                                                $593

                                                Price per night from

                                                $593

                                                Distance approx 3.91 km from Windermere

                                                  10

                                                  Lake Rosseau

                                                  Muskoka Lakes / Minett

                                                  Minett cottage

                                                  4 12 7 nights min

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

                                                  Price per night from

                                                  $1,145

                                                  Price per night from

                                                  $1,145

                                                  Distance approx 15.31 km from Windermere

                                                    6

                                                    Room with covered Porch and Cable by Falls in town

                                                    Muskoka District / Bracebridge

                                                    Bracebridge house

                                                    1 1 1 night min

                                                    • 1 bedroom
                                                    • sleeps 1
                                                    • 1 night min

                                                    Price per night from

                                                    $52

                                                    Responds fast!
                                                    avg. 7 minutes

                                                    Price per night from

                                                    $52

                                                    Distance approx 17.53 km from Windermere

                                                      44

                                                      Lakefront Treasure

                                                      Ontario / Kawartha Lakes

                                                      Kawartha Lakes cottage

                                                      3 8 7 nights min

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

                                                      Price per night from

                                                      $344

                                                      Price per night from

                                                      $344

                                                      Distance approx 17.21 km from Windermere

                                                      (3) Excellent 

                                                        23

                                                        Luxury Waterfront Cottage, Fox Lake in Huntsville

                                                        Muskoka District / Huntsville

                                                        Huntsville cottage

                                                        3 9 min stay varies

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

                                                        Price per night from

                                                        $413

                                                        Price per night from

                                                        $413

                                                        Distance approx 17.76 km from Windermere

                                                          9

                                                          Rocky Pines

                                                          Muskoka District / Muskoka Lakes

                                                          Muskoka Lakes house

                                                          3 8 7 nights min

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

                                                          Price per night from

                                                          $368

                                                          Price per night from

                                                          $368

                                                          Distance approx 19.28 km from Windermere

                                                            12

                                                            Cottage Rental on Beautiful Six Mile Lake

                                                            Muskoka District / Big Chute

                                                            Big Chute cottage

                                                            4 8 7 nights min

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

                                                            Price per night from

                                                            $246

                                                            Price per night from

                                                            $246

                                                            Distance approx 13.77 km from Windermere

                                                              14

                                                              Heavenly Cottage (Beautiful Lake Views)

                                                              Huntsville / Port Sydney

                                                              Port Sydney cottage

                                                              2 6 min stay varies

                                                              • 2 bedrooms
                                                              • sleeps 6
                                                              • min stay varies
                                                              • Child Friendly
                                                              • Air conditioning

                                                              Price per night from

                                                              $146

                                                              Price per night from

                                                              $146

                                                              Distance approx 8.6 km from Windermere

                                                                24

                                                                Lake Muskoka 4 BR Cottage, Sandy Beach, Sunny Decks, Private

                                                                Muskoka District / Muskoka Lakes

                                                                Muskoka Lakes cottage

                                                                4 10 min stay varies

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

                                                                Price per night from

                                                                $361

                                                                Price per night from

                                                                $361

                                                                Distance approx 16.47 km from Windermere

                                                                (3) Excellent 

                                                                  55

                                                                  Muskoka Luxury Cottage in Taboo Resort & Golf Club

                                                                  Muskoka District / Gravenhurst

                                                                  Gravenhurst cottage

                                                                  4 10 min stay varies

                                                                  • 4 bedrooms
                                                                  • sleeps 10
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Child Friendly
                                                                  • Air conditioning

                                                                  Price per night from

                                                                  $254

                                                                  Price per night from

                                                                  $254

                                                                  Distance approx 17.94 km from Windermere

                                                                    15

                                                                    Muskoka Luxury Cottage-Private- Beachfront- Dock & Toys

                                                                    Muskoka District / Gravenhurst

                                                                    Gravenhurst cottage

                                                                    4 8 3 nights min

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

                                                                    Price per night from

                                                                    $430

                                                                    Price per night from

                                                                    $430

                                                                    Distance approx 15.45 km from Windermere

                                                                    (80) Excellent 

                                                                      73

                                                                      Muskoka Soul * 5-Star Luxury Rentals * The Lake House

                                                                      Muskoka District / Gravenhurst

                                                                      Gravenhurst cottage

                                                                      5 10 min stay varies

                                                                      • 5 bedrooms
                                                                      • sleeps 10
                                                                      • min stay varies
                                                                      • Beach / lakeside relaxation
                                                                      • Nearest beach 6 mi
                                                                      • Child Friendly
                                                                      “Beautiful Muskoka!” We had a group of 10 up at Muskoka Soul in early January of 2014. It was a wonderful experience and the atmosphere was amazing. The facilities were spacious and the kitchen made it easy to prepare meals for a large group. There w
                                                                      …see more

                                                                      Price per night from

                                                                      $511

                                                                      Responds fast!
                                                                      avg. 49 minutes

                                                                      Price per night from

                                                                      $511

                                                                      Distance approx 5.59 km from Windermere

                                                                        8

                                                                        WHITE BIRCHES CAMP

                                                                        Northeastern Ontario / Port Loring

                                                                        Port Loring cottage

                                                                        2 4 7 nights min

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

                                                                        Price per night from

                                                                        $123

                                                                        Price per night from

                                                                        $123

                                                                        Distance approx 6.28 km from Windermere

                                                                        (8) Excellent 

                                                                          22

                                                                          The Hermitage

                                                                          Muskoka District / Muskoka Lakes

                                                                          Muskoka Lakes cottage

                                                                          6 12 7 nights min

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

                                                                          Price per night from

                                                                          $541

                                                                          Responds fast!
                                                                          avg. 3 hours 17 minutes

                                                                          Price per night from

                                                                          $541

                                                                          Distance approx 18.58 km from Windermere

                                                                            12

                                                                            Two Bedroom Cottage on Deer Lake RV Resort

                                                                            Muskoka District / Huntsville

                                                                            Huntsville cottage

                                                                            2 6 min stay varies

                                                                            • 2 bedrooms
                                                                            • sleeps 6
                                                                            • min stay varies
                                                                            • Ask about children
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $87

                                                                            Price per night from

                                                                            $87

                                                                            Distance approx 9.62 km from Windermere

                                                                              24

                                                                              Family Friendly Waterfront Property on Lake Joseph, Muskoka

                                                                              Muskoka District / Mactier

                                                                              Mactier cottage

                                                                              3 6 3 nights min

                                                                              • 3 bedrooms
                                                                              • sleeps 6
                                                                              • 3 nights min
                                                                              • Ski
                                                                              • Child Friendly
                                                                              • Pet Friendly

                                                                              Price per night from

                                                                              $441

                                                                              Price per night from

                                                                              $441