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61 Houses

(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

    (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

      (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

        (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

          Price per night from

          $356

            5

            Murmuring Maples

            Ontario / Orillia

            Orillia house

            1 2 1 night min

            • 1 bedroom
            • sleeps 2
            • 1 night min
            • Air conditioning
            • Private garden

            Price per night from

            $48

            Price per night from

            $48

              10

              The Nut House-Forest in the city- 4 bedrooms

              Ontario / Orillia

              Orillia house

              4 8 7 nights min

              • 4 bedrooms
              • sleeps 8
              • 7 nights min

              Price per night from

              $172

              Price per night from

              $172

                43

                Luxury Cottage On Lake Simcoe SLEEPS 16+

                Ontario / Orillia

                Orillia house

                6 16 3 nights min

                • 6 bedrooms
                • sleeps 16
                • 3 nights min
                • Child Friendly
                • Air conditioning
                • Private garden

                Price per night from

                $859

                Price per night from

                $859

                (1) Excellent 

                  7

                  Simcoe Lake House Oasis

                  Ontario / Orillia

                  Orillia house

                  6 16 3 nights min

                  • 6 bedrooms
                  • sleeps 16
                  • 3 nights min
                  • Child Friendly

                  Price per night from

                  $859

                  Price per night from

                  $859

                  Great rentals within 20 miles that match your search

                  Distance approx 11.58 km from Orillia Show on Map

                    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 12.33 km from Orillia Show on Map

                      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 9.28 km from Orillia Show on Map

                      (3) 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. 31 minutes

                        Price per night from

                        $215

                        Distance approx 19.86 km from Orillia Show on Map

                          13

                          Tuckmee Inn Bed and Breakfast - Forest Room

                          Georgina / Sutton

                          Sutton house

                          1 2 1 night min

                          • 1 bedroom
                          • sleeps 2
                          • 1 night min
                          • Nearest beach 2 mi
                          • Air conditioning
                          • Private garden

                          Price per night from

                          $82

                          Price per night from

                          $82

                          Distance approx 19.73 km from Orillia Show on Map

                            9

                            5 BR Cottage in Kirkfield, 30 Min Oshawa, Near Casino Rama, 20 Slps, Year Round

                            Kawartha Lakes / Kirkfield

                            Kirkfield cottage

                            5 20 1 night min

                            • 5 bedrooms
                            • sleeps 20
                            • 1 night min
                            • Child Friendly
                            • Air conditioning
                            • Pet Friendly

                            Price per night from

                            $162

                            Price per night from

                            $162

                            Distance approx 12.92 km from Orillia Show on Map

                              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 18.19 km from Orillia Show on Map

                                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 10.75 km from Orillia Show on Map

                                  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 16.29 km from Orillia Show on Map

                                  (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 12.92 km from Orillia Show on Map

                                      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 8.46 km from Orillia Show on Map

                                      (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. 31 minutes

                                        Price per night from

                                        $258

                                        Distance approx 16.72 km from Orillia Show on Map

                                        (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

                                          $280

                                          Responds fast!
                                          avg. 28 minutes

                                          Price per night from

                                          $280

                                          Distance approx 19.74 km from Orillia Show on Map

                                          (1) Excellent 

                                            13

                                            Lake Simcoe-- Jacksons Pt

                                            Georgina / Jacksons Point

                                            Jacksons Point cottage

                                            6 10 3 nights min

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

                                            Price per night from

                                            $258

                                            Price per night from

                                            $258

                                            Distance approx 12.92 km from Orillia Show on Map

                                              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 19.88 km from Orillia Show on Map

                                              (2)  

                                                14

                                                The LakeShore- Jackson's Point-Georgina, Ontario

                                                Georgina / Sutton

                                                Sutton cottage

                                                3 7 2 nights min

                                                • 3 bedrooms
                                                • sleeps 7
                                                • 2 nights min
                                                • Beach / lakeside relaxation
                                                • Child Friendly
                                                • Car not necessary

                                                Price per night from

                                                $112

                                                Responds fast!
                                                avg. 1 hour 21 minutes

                                                Price per night from

                                                $112

                                                Distance approx 19.77 km from Orillia Show on Map

                                                  8

                                                  Small, Comfy Cottage In Kawartha Lakes, 6 Sleeps, Year Round

                                                  Kawartha Lakes / Kirkfield

                                                  Kirkfield cottage

                                                  2 6 1 night min

                                                  • 2 bedrooms
                                                  • sleeps 6
                                                  • 1 night min
                                                  • Child Friendly
                                                  • Air conditioning

                                                  Price per night from

                                                  $189

                                                  Price per night from

                                                  $189

                                                  Distance approx 15.99 km from Orillia Show on Map

                                                  (1) Excellent 

                                                    14

                                                    Carriage Hills Resort Two-Bedroom Suite

                                                    Oro Station / Shanty Bay

                                                    Shanty Bay condo

                                                    2 8 7 nights min

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

                                                    Price per night from

                                                    $258

                                                    Price per night from

                                                    $258

                                                    Distance approx 11.49 km from Orillia Show on Map

                                                      29

                                                      lakeside cottage by lake Simcoe

                                                      Ontario / Brechin

                                                      Brechin house

                                                      5 12 2 nights min

                                                      • 5 bedrooms
                                                      • sleeps 12
                                                      • 2 nights min
                                                      • Child Friendly
                                                      • Pet Friendly
                                                      • Private garden

                                                      Price per night from

                                                      $516

                                                      Responds fast!
                                                      avg. 17 minutes

                                                      Price per night from

                                                      $516

                                                      Distance approx 11.07 km from Orillia Show on Map

                                                      (1) Very Good 

                                                        63

                                                        Family Cottage for rent

                                                        Ontario / Brechin

                                                        Brechin cottage

                                                        3 8 min stay varies

                                                        • 3 bedrooms
                                                        • sleeps 8
                                                        • min stay varies
                                                        • Nearest beach 0.3 mi
                                                        • Child Friendly

                                                        Price per night from

                                                        $301

                                                        Price per night from

                                                        $301

                                                        Distance approx 6.33 km from Orillia Show on Map

                                                          7

                                                          Ravens Ridge Bed and Breakfast Rose Garden

                                                          Ontario / Oro-Medonte

                                                          Oro-Medonte b and b

                                                          1 2 1 night min

                                                          • 1 bedroom
                                                          • sleeps 2
                                                          • 1 night min
                                                          • Nearest beach 10 mi
                                                          • Air conditioning
                                                          • Private garden

                                                          Price per night from

                                                          $128

                                                          Price per night from

                                                          $128

                                                          Distance approx 18.89 km from Orillia Show on Map

                                                            46

                                                            Luxury Accommodation At A Reasonable Price

                                                            Ontario / Barrie

                                                            Barrie b and b

                                                            2 4 2 nights min

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

                                                            Price per night from

                                                            $258

                                                            Price per night from

                                                            $258

                                                            Distance approx 6.37 km from Orillia Show on Map

                                                              5

                                                              Ravens Ridge Bed and Breakfast Sweet Dreams

                                                              Ontario / Oro-Medonte

                                                              Oro-Medonte b and b

                                                              1 2 1 night min

                                                              • 1 bedroom
                                                              • sleeps 2
                                                              • 1 night min

                                                              Price per night from

                                                              $128

                                                              Price per night from

                                                              $128

                                                              Distance approx 12.93 km from Orillia Show on Map

                                                                4

                                                                Ski Spring Break!

                                                                Ontario / Horseshoe Valley

                                                                Horseshoe Valley villa

                                                                1 4 6 nights min

                                                                • 1 bedroom
                                                                • sleeps 4
                                                                • 6 nights min
                                                                • Swimming pool
                                                                • Ski
                                                                • Child Friendly

                                                                Price per night from

                                                                $112

                                                                Price per night from

                                                                $112

                                                                Distance approx 13.48 km from Orillia Show on Map

                                                                  18

                                                                  == February 10-17 == Holiday week == Luxury resort == ski lift at door

                                                                  Ontario / Barrie

                                                                  Barrie villa

                                                                  2 8 7 nights min

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

                                                                  Price per night from

                                                                  $266

                                                                  Price per night from

                                                                  $266

                                                                  Distance approx 12.92 km from Orillia Show on Map

                                                                  (1) Excellent 

                                                                    9

                                                                    Carriage Hills Resort Fabulous 2 br sleep8

                                                                    Oro Station / Shanty Bay

                                                                    Shanty Bay condo

                                                                    2 8 7 nights min

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

                                                                    Price per night from

                                                                    $141

                                                                    Price per night from

                                                                    $141

                                                                    Distance approx 11.39 km from Orillia Show on Map

                                                                      6

                                                                      Room bachelor ensuite

                                                                      Ontario / Brechin

                                                                      Brechin house

                                                                      1 2 2 nights min

                                                                      • 1 bedroom
                                                                      • sleeps 2
                                                                      • 2 nights min
                                                                      • Air conditioning
                                                                      • Private garden

                                                                      Price per night from

                                                                      $35

                                                                      Responds fast!
                                                                      avg. 1 hour 41 minutes

                                                                      Price per night from

                                                                      $35

                                                                      Distance approx 17.9 km from Orillia Show on Map

                                                                        11

                                                                        Modern Cottage w/ Hot Tub, Sunset Lake View, Trail

                                                                        Ontario / Waubaushene

                                                                        Waubaushene cottage

                                                                        4 8 2 nights min

                                                                        • 4 bedrooms
                                                                        • sleeps 8
                                                                        • 2 nights min
                                                                        • Child Friendly
                                                                        • Pet Friendly

                                                                        Price per night from

                                                                        $258

                                                                        Price per night from

                                                                        $258

                                                                        Distance approx 11.47 km from Orillia Show on Map

                                                                          9

                                                                          Condo for rent

                                                                          Ontario / Brechin

                                                                          Brechin villa

                                                                          2 6 3 nights min

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

                                                                          Price per night from

                                                                          $112

                                                                          Responds fast!
                                                                          avg. 1 hour 41 minutes

                                                                          Price per night from

                                                                          $112

                                                                          Distance approx 11.56 km from Orillia Show on Map

                                                                          (2) Very Good 

                                                                            11

                                                                            Vacational rental, short or long term rental

                                                                            Ontario / Brechin

                                                                            Brechin villa

                                                                            2 4 2 nights min

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

                                                                            Price per night from

                                                                            $86

                                                                            Responds fast!
                                                                            avg. 1 hour 41 minutes

                                                                            Price per night from

                                                                            $86

                                                                            Distance approx 6.01 km from Orillia Show on Map

                                                                              5

                                                                              Home away from home

                                                                              Ontario / Severn

                                                                              Severn house

                                                                              2 6 2 nights min

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

                                                                              Price per night from

                                                                              $129

                                                                              Responds fast!
                                                                              avg. 3 hours 17 minutes

                                                                              Price per night from

                                                                              $129