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38 Houses

Great rentals within 20 miles that match your search

Distance approx 18.77 km from Cumberland Beach

    8

    All Season Retreat on Lake Simcoe

    Ontario / Oro Station

    Oro Station cottage

    2 5 min stay varies

    • 2 bedrooms
    • sleeps 5
    • min stay varies
    • Beach / lakeside relaxation
    • Ask about children
    • Pet Friendly

    Price per night from

    $171

    Price per night from

    $171

    Distance approx 15.54 km from Cumberland Beach

      14

      Fabulous Loon Lake

      Muskoka District / Gravenhurst

      Gravenhurst cottage

      3 6 30 nights min

      • 3 bedrooms
      • sleeps 6
      • 30 nights min
      • Beach / lakeside relaxation
      • Child Friendly

      Price per night from

      $302

      Price per night from

      $302

      Distance approx 18.05 km from Cumberland Beach

        14

        Lake Simcoe Lake House

        Ontario / Oro Station

        Oro Station house

        2 8 3 nights min

        • 2 bedrooms
        • sleeps 8
        • 3 nights min
        • Beach / lakeside relaxation
        • Child Friendly
        • Pet Friendly

        Price per night from

        $301

        Price per night from

        $301

        Distance approx 18.17 km from Cumberland Beach

        (8) Excellent 

          16

          Georgian Bay Cottage Vacations

          Ontario / Victoria Harbour

          Victoria Harbour cottage

          3 6 3 nights min

          • 3 bedrooms
          • sleeps 6
          • 3 nights min
          • Beach / lakeside relaxation
          • Ski
          • Child Friendly

          Price per night from

          $301

          Price per night from

          $301

          Distance approx 13.45 km from Cumberland Beach

            31

            Waterfront on Paradise with amazing views

            Ontario / Brechin

            Brechin house

            3 10 min stay varies

            • 3 bedrooms
            • sleeps 10
            • min stay varies
            • Child Friendly

            Price per night from

            $460

            Price per night from

            $460

            Distance approx 17.29 km from Cumberland Beach

              6

              Walk Out & Ski!!

              Ontario / Horseshoe Valley

              Horseshoe Valley condo

              2 6 6 nights min

              • 2 bedrooms
              • sleeps 6
              • 6 nights min
              • Ski
              • Child Friendly

              Price per night from

              $229

              Price per night from

              $229

              Distance approx 5.19 km from Cumberland Beach Show on Map

                32

                Country Charm -1

                Ontario / Severn Bridge

                Severn Bridge house

                2 2 2 nights min

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

                Price per night from

                $75

                Responds fast!
                avg. 2 hours 16 minutes

                Price per night from

                $75

                Distance approx 5.19 km from Cumberland Beach Show on Map

                (3) Excellent 

                  13

                  Country Charm - 2

                  Ontario / Severn Bridge

                  Severn Bridge house

                  3 3 1 night min

                  • 3 bedrooms
                  • sleeps 3
                  • 1 night min
                  • Nearest beach 10 mi
                  • Air conditioning
                  • Private garden

                  Price per night from

                  $75

                  Responds fast!
                  avg. 2 hours 16 minutes

                  Price per night from

                  $75

                  Distance approx 16.37 km from Cumberland Beach

                    10

                    Executive family cottage

                    Oro Station / Shanty Bay

                    Shanty Bay bungalow

                    3 8 3 nights min

                    • 3 bedrooms
                    • sleeps 8
                    • 3 nights min
                    • Child Friendly
                    • Air conditioning
                    • Private garden

                    Price per night from

                    $258

                    Responds fast!
                    avg. 24 minutes

                    Price per night from

                    $258

                    Distance approx 18.92 km from Cumberland Beach

                    (2) Excellent 

                      21

                      Cozy cottage serenely nestled between Talbot River and the Trent-Severn Waterway

                      Ontario / Beaverton

                      Beaverton cottage

                      3 6 min stay varies

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

                      Price per night from

                      $237

                      Price per night from

                      $237

                      Distance approx 14.97 km from Cumberland Beach

                      (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 13.48 km from Cumberland Beach

                        (2) Excellent 

                          34

                          Horseshoe Valley Farm

                          Ontario / Horseshoe Valley

                          Horseshoe Valley farmhouse

                          3 7 2 nights min

                          • 3 bedrooms
                          • sleeps 7
                          • 2 nights min
                          • Nearest beach 8 mi
                          • Ski
                          • Child Friendly

                          Price per night from

                          $215

                          Responds fast!
                          avg. 33 minutes

                          Price per night from

                          $215

                          Distance approx 15.46 km from Cumberland Beach

                            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 17.29 km from Cumberland Beach

                              19

                              Carriage Ridge Resort 2 bedroom suite

                              Oro Station / Shanty Bay

                              Shanty Bay apartment

                              2 8 7 nights min

                              • 2 bedrooms
                              • sleeps 8
                              • 7 nights min
                              • Swimming pool
                              • Child Friendly
                              • Air conditioning

                              Price per night from

                              $258

                              Price per night from

                              $258

                              Distance approx 19.73 km from Cumberland Beach

                                20

                                Brand new cottage. Can Accommodate 6 People

                                Ontario / Beaverton

                                Beaverton cottage

                                4 6 7 nights min

                                • 4 bedrooms
                                • sleeps 6
                                • 7 nights min
                                • Child Friendly
                                • Air conditioning
                                • Private garden

                                Price per night from

                                $307

                                Price per night from

                                $307

                                Distance approx 12.84 km from Cumberland Beach

                                  21

                                  Ye Old Country Store Inn Enjoy Ski & Lake Country in Canada

                                  Ontario / Oro Station

                                  Oro Station chateau

                                  3 10 2 nights min

                                  • 3 bedrooms
                                  • sleeps 10
                                  • 2 nights min
                                  • Nearest beach 5 mi
                                  • Child Friendly
                                  • Air conditioning

                                  Price per night from

                                  $194

                                  Responds fast!
                                  avg. 1 hour 56 minutes

                                  Price per night from

                                  $194

                                  Distance approx 18.34 km from Cumberland Beach

                                  (9) Excellent 

                                    32

                                    Muskoka Rocks Lake Muskoka

                                    Muskoka District / Muskoka Lakes

                                    Muskoka Lakes cottage

                                    3 8 min stay varies

                                    • 3 bedrooms
                                    • sleeps 8
                                    • min stay varies
                                    • Beach / lakeside relaxation
                                    • Child Friendly
                                    • Private garden

                                    Price per night from

                                    $429

                                    Price per night from

                                    $429

                                    Distance approx 0.1 km from Cumberland Beach Show on Map

                                    (3) Very Good 

                                      35

                                      Leaning Tree Cottage

                                      Ontario / Orillia

                                      Orillia cottage

                                      3 10 3 nights min

                                      • 3 bedrooms
                                      • sleeps 10
                                      • 3 nights min
                                      • Beach / lakeside relaxation
                                      • Nearest beach 1 mi
                                      • Child Friendly

                                      Price per night from

                                      $171

                                      Price per night from

                                      $171

                                      Distance approx 17.99 km from Cumberland Beach

                                        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 16.77 km from Cumberland Beach

                                        (1) Excellent 

                                          12

                                          Cozy Chalet in Horseshoe Valley

                                          Ontario / Horseshoe Valley

                                          Horseshoe Valley house

                                          4 10 2 nights min

                                          • 4 bedrooms
                                          • sleeps 10
                                          • 2 nights min
                                          • Child Friendly
                                          • Ask about pets
                                          • Private garden

                                          Price per night from

                                          $280

                                          Price per night from

                                          $280

                                          Distance approx 7.41 km from Cumberland Beach Show on Map

                                          (73) Very Good 

                                          Certificate of Excellence

                                            65

                                            Trenanthia Cottage (Hot Tub, Sauna, Games Room, Log Fireplaces, Sandy Beach++)

                                            Muskoka District / Gravenhurst

                                            Gravenhurst cottage

                                            5 12 min stay varies

                                            • 5 bedrooms
                                            • sleeps 12
                                            • min stay varies
                                            • Beach / lakeside relaxation
                                            • Nearest beach 0 mi
                                            • Child Friendly
                                            “Perfect family get together.” We visited Trenanthia cottage to celebrate my grandmother's 90th birthday, the location needed to suit all of our party ranging in ages from 4 years to 90 years old. The cottage did not disappoint, plenty of space for eve
                                            …see more

                                            Certificate of Excellence

                                            Price per night from

                                            $132

                                            Responds fast!
                                            avg. 1 hour 32 minutes

                                            Price per night from

                                            $132

                                            Distance approx 13.86 km from Cumberland Beach

                                              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

                                              Price per night from

                                              $260

                                              Distance approx 14.52 km from Cumberland Beach

                                              (2) Excellent 

                                                17

                                                Cottages and Boats to rent

                                                Ontario / Orillia

                                                Orillia cottage

                                                2 4 2 nights min

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

                                                Price per night from

                                                $155

                                                Price per night from

                                                $155

                                                Distance approx 13.27 km from Cumberland Beach

                                                (2) Excellent 

                                                  29

                                                  Post and beam with hot tub and sauna 20 minutes to ski hills, beaches and casino

                                                  Ontario / Coldwater

                                                  Coldwater house

                                                  4 10 2 nights min

                                                  • 4 bedrooms
                                                  • sleeps 10
                                                  • 2 nights min
                                                  • Child Friendly
                                                  • Air conditioning
                                                  • Pet Friendly

                                                  Price per night from

                                                  $258

                                                  Responds fast!
                                                  avg. 1 hour 58 minutes

                                                  Price per night from

                                                  $258

                                                  Distance approx 12.19 km from Cumberland Beach

                                                  (4) Excellent 

                                                    23

                                                    Horseshoe Valley Fieldview Farm

                                                    Ontario / Horseshoe Valley

                                                    Horseshoe Valley farmhouse

                                                    5 12 2 nights min

                                                    • 5 bedrooms
                                                    • sleeps 12
                                                    • 2 nights min
                                                    • Nearest beach 8 mi
                                                    • Child Friendly
                                                    • Pet Friendly

                                                    Price per night from

                                                    $258

                                                    Responds fast!
                                                    avg. 33 minutes

                                                    Price per night from

                                                    $258

                                                    Distance approx 15.77 km from Cumberland Beach

                                                    (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 3.85 km from Cumberland Beach Show on Map

                                                      (1) Excellent 

                                                        12

                                                        Family Cottage Escape on Lake Couchiching

                                                        Ontario / Orillia

                                                        Orillia cottage

                                                        4 8 3 nights min

                                                        • 4 bedrooms
                                                        • sleeps 8
                                                        • 3 nights min
                                                        • Beach / lakeside relaxation
                                                        • Ask about children
                                                        • Air conditioning

                                                        Price per night from

                                                        $237

                                                        Price per night from

                                                        $237

                                                        Distance approx 14.37 km from Cumberland Beach

                                                          15

                                                          Golf Villa for Rent inside Muskoka Bay Club

                                                          Muskoka District / Gravenhurst

                                                          Gravenhurst villa

                                                          1 5 2 nights min

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

                                                          Price per night from

                                                          $215

                                                          Responds fast!
                                                          avg. 2 hours 25 minutes

                                                          Price per night from

                                                          $215

                                                          Distance approx 8.51 km from Cumberland Beach Show on Map

                                                          (1) Very Good 

                                                            6

                                                            EXECUTIVE WATERFRONT ON BASS LAKE ORILLIA -SUMMER!

                                                            Ontario / Orillia

                                                            Orillia cottage

                                                            4 8 7 nights min

                                                            • 4 bedrooms
                                                            • sleeps 8
                                                            • 7 nights min
                                                            • Beach / lakeside relaxation
                                                            • Nearest beach 0.8 mi
                                                            • Child Friendly

                                                            Price per night from

                                                            $356

                                                            Responds fast!
                                                            avg. 2 hours 25 minutes

                                                            Price per night from

                                                            $356

                                                            Distance approx 17.53 km from Cumberland Beach

                                                            (3) Very Good 

                                                              7

                                                              Small family cottage for rent

                                                              Muskoka District / Port Severn

                                                              Port Severn cottage

                                                              2 6 7 nights min

                                                              • 2 bedrooms
                                                              • sleeps 6
                                                              • 7 nights min
                                                              • Child Friendly
                                                              • Pet Friendly

                                                              Price per night from

                                                              $117

                                                              Responds fast!
                                                              avg. 1 hour 42 minutes

                                                              Price per night from

                                                              $117

                                                              Distance approx 5.25 km from Cumberland Beach Show on Map

                                                                12

                                                                Cabin for 2 light breakfast

                                                                Ontario / Severn Bridge

                                                                Severn Bridge guest house

                                                                1 2 1 night min

                                                                • 1 bedroom
                                                                • sleeps 2
                                                                • 1 night min
                                                                • Pet Friendly
                                                                • Private garden

                                                                Price per night from

                                                                $95

                                                                Responds fast!
                                                                avg. 2 hours 16 minutes

                                                                Price per night from

                                                                $95

                                                                Distance approx 6.18 km from Cumberland Beach Show on Map

                                                                (3) Very Good 

                                                                  23

                                                                  Clean Picturesque Boater Paradise

                                                                  Ontario / Severn

                                                                  Severn condo

                                                                  3 8 2 nights min

                                                                  • 3 bedrooms
                                                                  • sleeps 8
                                                                  • 2 nights min
                                                                  • Nearest beach 10 mi
                                                                  • Child Friendly
                                                                  • Pet Friendly

                                                                  Price per night from

                                                                  $129

                                                                  Responds fast!
                                                                  avg. 3 hours 32 minutes

                                                                  Price per night from

                                                                  $129

                                                                  Distance approx 5.2 km from Cumberland Beach Show on Map

                                                                    16

                                                                    Country Charm - 4

                                                                    Ontario / Severn Bridge

                                                                    Severn Bridge house

                                                                    4 3 2 nights min

                                                                    • 4 bedrooms
                                                                    • sleeps 3
                                                                    • 2 nights min
                                                                    • Child Friendly
                                                                    • Private garden

                                                                    Price per night from

                                                                    $92

                                                                    Responds fast!
                                                                    avg. 2 hours 16 minutes

                                                                    Price per night from

                                                                    $92

                                                                    Distance approx 17.29 km from Cumberland Beach

                                                                      6

                                                                      Skyiing vacation in the mountains

                                                                      Oro Station / Shanty Bay

                                                                      Shanty Bay house

                                                                      1 4 7 nights min

                                                                      • 1 bedroom
                                                                      • sleeps 4
                                                                      • 7 nights min
                                                                      • Swimming pool
                                                                      • Child Friendly
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $92

                                                                      Price per night from

                                                                      $92

                                                                      Distance approx 6.94 km from Cumberland Beach Show on Map

                                                                        6

                                                                        Cottages at Pt Stanton 2bdrm

                                                                        Muskoka District / Gravenhurst

                                                                        Gravenhurst cottage

                                                                        2 8 7 nights min

                                                                        • 2 bedrooms
                                                                        • sleeps 8
                                                                        • 7 nights min
                                                                        • Swimming pool
                                                                        • Child Friendly
                                                                        • Air conditioning

                                                                        Price per night from

                                                                        $295

                                                                        Price per night from

                                                                        $295

                                                                        Distance approx 5.96 km from Cumberland Beach Show on Map

                                                                          25

                                                                          Waterfront Vacation in Luxury

                                                                          Ontario / Severn Bridge

                                                                          Severn Bridge cottage

                                                                          4 10 7 nights min

                                                                          • 4 bedrooms
                                                                          • sleeps 10
                                                                          • 7 nights min
                                                                          • Child Friendly
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $430

                                                                          Price per night from

                                                                          $430

                                                                          Distance approx 18.07 km from Cumberland Beach

                                                                            4

                                                                            Lakeridge - Gorgeous Cape Cod in South Muskoka

                                                                            Muskoka District / Port Severn

                                                                            Port Severn cottage

                                                                            6 10 2 nights min

                                                                            • 6 bedrooms
                                                                            • sleeps 10
                                                                            • 2 nights min
                                                                            • Child Friendly
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $688

                                                                            Price per night from

                                                                            $688

                                                                            Distance approx 16.19 km from Cumberland Beach

                                                                            (3) Excellent 

                                                                              6

                                                                              Even Kiehl Bed & Breakfast

                                                                              Muskoka District / Gravenhurst

                                                                              Gravenhurst b and b

                                                                              1 2 1 night min

                                                                              • 1 bedroom
                                                                              • sleeps 2
                                                                              • 1 night min
                                                                              • Nearest beach 2 mi
                                                                              • Child Friendly
                                                                              • Pet Friendly

                                                                              Price per night from

                                                                              $121

                                                                              Responds fast!
                                                                              avg. 3 hours 42 minutes

                                                                              Price per night from

                                                                              $121