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62 Houses

(3) Excellent 

    35

    Charlotte's Cottage-Lake Simcoe

    Georgina / Keswick

    Keswick cottage

    2 6 7 nights min

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

    Price per night from

    $137

    Responds fast!
    avg. 52 minutes

    Price per night from

    $137

    (1) Excellent 

      16

      Georgina Lakeshore Vacation Home

      Georgina / Keswick

      Keswick house

      3 10 2 nights min

      • 3 bedrooms
      • sleeps 10
      • 2 nights min
      • Swimming pool
      • Child Friendly
      • Air conditioning

      Price per night from

      $197

      Responds fast!
      avg. 2 hours 10 minutes

      Price per night from

      $197

      (5) Excellent 

        23

        Exquisite Executive Cottage on Lake Simcoe

        Georgina / Keswick

        Keswick house

        4 14 2 nights min

        • 4 bedrooms
        • sleeps 14
        • 2 nights min
        • Beach / lakeside relaxation
        • Child Friendly
        • Air conditioning

        Price per night from

        $513

        Price per night from

        $513

          49

          Tex’s Beautiful Cottage & Private Beach

          Georgina / Keswick

          Keswick cottage

          6 22 2 nights min

          • 6 bedrooms
          • sleeps 22
          • 2 nights min
          • Child Friendly

          Price per night from

          $598

          Price per night from

          $598

          Great rentals within 20 miles that match your search

          Distance approx 3.54 km from Keswick Show on Map

          (1)  

            18

            Lakefront home on Lake Simcoe

            Ontario / Innisfil

            Innisfil house

            4 10 7 nights min

            • 4 bedrooms
            • sleeps 10
            • 7 nights min
            • Beach / lakeside relaxation
            • Ask about children
            • Air conditioning

            Price per night from

            $733

            Price per night from

            $733

            Distance approx 19.85 km from Keswick

              7

              Ravens Ridge Bed and Breakfast River Rock Suite

              Ontario / Oro-Medonte

              Oro-Medonte b and b

              1 2 1 night min

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

              Price per night from

              $111

              Price per night from

              $111

              Distance approx 15.13 km from Keswick

              (4) Excellent 

                69

                LAKE SIMCOE'S L'IL COTTAGE MEXICO IN CANADA

                Ontario / Barrie

                Barrie cottage

                4 12 7 nights min

                • 4 bedrooms
                • sleeps 12
                • 7 nights min
                • Beach / lakeside relaxation
                • Nearest beach 0 mi
                • Child Friendly

                Price per night from

                $513

                Price per night from

                $513

                Distance approx 14.6 km from Keswick

                  7

                  South Side Bed and Breakfast

                  Ontario / Barrie

                  Barrie b and b

                  1 2 1 night min

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

                  Price per night from

                  $129

                  Price per night from

                  $129

                  Distance approx 15.67 km from Keswick

                    24

                    2 Bedroom-Downtown Lake view Penthouse

                    Ontario / Barrie

                    Barrie apartment

                    2 4 4 nights min

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

                    Price per night from

                    $150

                    Price per night from

                    $150

                    Distance approx 8.39 km from Keswick Show on Map

                      12

                      Waterfront Cottage Hideaway on Lake Simcoe

                      Ontario / Innisfil

                      Innisfil house

                      2 7 5 nights min

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

                      Price per night from

                      $213

                      Price per night from

                      $213

                      Distance approx 6.89 km from Keswick Show on Map

                      (1) Excellent 

                        19

                        3brm cottage with hot tub and sauna

                        Ontario / Innisfil

                        Innisfil bungalow

                        3 8 2 nights min

                        • 3 bedrooms
                        • sleeps 8
                        • 2 nights min
                        • Beach / lakeside relaxation
                        • Nearest beach 0.5 mi
                        • Child Friendly

                        Price per night from

                        $146

                        Price per night from

                        $146

                        Distance approx 8.8 km from Keswick

                          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 12.2 km from Keswick

                            24

                            Stunning Big Bay Point Lake House

                            Ontario / Innisfil

                            Innisfil house

                            4 8 4 nights min

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

                            Price per night from

                            $513

                            Responds fast!
                            avg. 54 minutes

                            Price per night from

                            $513

                            Distance approx 19.85 km from Keswick

                              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 14.49 km from Keswick

                                7

                                2 bedroom cottage on Lake Simcoe

                                Ontario / Toronto

                                Toronto cottage

                                2 6 2 nights min

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

                                Price per night from

                                $300

                                Price per night from

                                $300

                                Distance approx 16.72 km from Keswick

                                  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

                                  $257

                                  Responds fast!
                                  avg. 18 minutes

                                  Price per night from

                                  $257

                                  Distance approx 11.96 km from Keswick

                                    25

                                    Fabulous Stylish 3 bedroom

                                    Ontario / Newmarket

                                    Newmarket house

                                    3 7 3 nights min

                                    • 3 bedrooms
                                    • sleeps 7
                                    • 3 nights min
                                    • Child Friendly
                                    • Air conditioning

                                    Price per night from

                                    $129

                                    Price per night from

                                    $129

                                    Distance approx 12.57 km from Keswick

                                    (1) Average 

                                      10

                                      Furnished modern 2 bedroom executive lease

                                      Ontario / Barrie

                                      Barrie house

                                      2 3 14 nights min

                                      • 2 bedrooms
                                      • sleeps 3
                                      • 14 nights min
                                      • Child Friendly

                                      Price per night from

                                      $68

                                      Responds fast!
                                      avg. 3 hours 10 minutes

                                      Price per night from

                                      $68

                                      Distance approx 7.34 km from Keswick Show on Map

                                      (4) Excellent 

                                        34

                                        Alfa Getaway ( Tuscan style)

                                        Ontario / Innisfil

                                        Innisfil cottage

                                        1 3 2 nights min

                                        • 1 bedroom
                                        • sleeps 3
                                        • 2 nights min
                                        • Beach / lakeside relaxation
                                        • Child Friendly
                                        • Air conditioning

                                        Price per night from

                                        $82

                                        Responds fast!
                                        avg. 1 hour 45 minutes

                                        Price per night from

                                        $82

                                        Distance approx 14.27 km from Keswick

                                          10

                                          Georgian Country Guesthouse minutes to Lake Simcoe

                                          Georgina / Jacksons Point

                                          Jacksons Point guest house

                                          1 2 2 nights min

                                          • 1 bedroom
                                          • sleeps 2
                                          • 2 nights min

                                          Price per night from

                                          $90

                                          Price per night from

                                          $90

                                          Distance approx 14.63 km from Keswick

                                            7

                                            A Brand New Rental Room available in South Barrie

                                            Ontario / Barrie

                                            Barrie house

                                            1 1 30 nights min

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

                                            Price per night from

                                            $26

                                            Price per night from

                                            $26

                                            Distance approx 5.31 km from Keswick Show on Map

                                              12

                                              Cozy Cottage

                                              Ontario / Georgina

                                              Georgina cottage

                                              2 6 7 nights min

                                              • 2 bedrooms
                                              • sleeps 6
                                              • 7 nights min

                                              Price per night from

                                              $123

                                              Price per night from

                                              $123

                                              Distance approx 8.8 km from Keswick

                                                13

                                                Tuckmee Inn Bed and Breakfast- Birch 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 11.96 km from Keswick

                                                  22

                                                  Spectacular Apartment in Newmarket, Ontario

                                                  Ontario / Newmarket

                                                  Newmarket apartment

                                                  1 2 2 nights min

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

                                                  Price per night from

                                                  $65

                                                  Price per night from

                                                  $65

                                                  Distance approx 6.41 km from Keswick Show on Map

                                                  (1) Very Good 

                                                    11

                                                    Guest House by Franklin Beach

                                                    Georgina / Sutton

                                                    Sutton house

                                                    4 18 1 night min

                                                    • 4 bedrooms
                                                    • sleeps 18
                                                    • 1 night min
                                                    • Child Friendly
                                                    • Air conditioning
                                                    • Pet Friendly

                                                    Price per night from

                                                    $427

                                                    Price per night from

                                                    $427

                                                    Distance approx 9.98 km from Keswick

                                                      9

                                                      Bradford Vacation

                                                      Ontario / Newmarket

                                                      Newmarket apartment

                                                      2 3 1 night min

                                                      • 2 bedrooms
                                                      • sleeps 3
                                                      • 1 night min
                                                      • Child Friendly

                                                      Price per night from

                                                      $77

                                                      Price per night from

                                                      $77

                                                      Distance approx 15.69 km from Keswick

                                                      (1) Excellent 

                                                        39

                                                        Trendi Suites "The Island"

                                                        Ontario / Barrie

                                                        Barrie house

                                                        3 6 min stay varies

                                                        • 3 bedrooms
                                                        • sleeps 6
                                                        • min stay varies
                                                        • Nearest beach 2 mi
                                                        • Child Friendly
                                                        • Air conditioning

                                                        Price per night from

                                                        $129

                                                        Price per night from

                                                        $129

                                                        Distance approx 13.17 km from Keswick

                                                          15

                                                          Private apt with deck and private yard

                                                          Ontario / Newmarket

                                                          Newmarket apartment

                                                          1 4 1 night min

                                                          • 1 bedroom
                                                          • sleeps 4
                                                          • 1 night min
                                                          • Nearest beach 20 mi
                                                          • Child Friendly
                                                          • Car not necessary

                                                          Price per night from

                                                          $103

                                                          Price per night from

                                                          $103

                                                          Distance approx 6.94 km from Keswick Show on Map

                                                            9

                                                            Cottage with hot tub and sauna

                                                            Innisfil / Cookstown

                                                            Cookstown house

                                                            3 8 2 nights min

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

                                                            Price per night from

                                                            $146

                                                            Price per night from

                                                            $146

                                                            Distance approx 13.31 km from Keswick

                                                            (2) Excellent 

                                                              17

                                                              Barrie. Very very private 4 acres, Whole Property

                                                              Ontario / Barrie

                                                              Barrie house

                                                              4 16 2 nights min

                                                              • 4 bedrooms
                                                              • sleeps 16
                                                              • 2 nights min
                                                              • Child Friendly
                                                              • Private garden

                                                              Price per night from

                                                              $342

                                                              Responds fast!
                                                              avg. 1 hour 23 minutes

                                                              Price per night from

                                                              $342

                                                              Distance approx 13.28 km from Keswick

                                                              (6) Very Good 

                                                                23

                                                                NEWMARKET - 30 minutes north of Toronto near Ontario's vacationland!

                                                                Ontario / Newmarket

                                                                Newmarket house

                                                                1 9 7 nights min

                                                                • 1 bedroom
                                                                • sleeps 9
                                                                • 7 nights min
                                                                • Nearest beach 30 mi
                                                                • Swimming pool
                                                                • Air conditioning

                                                                Price per night from

                                                                $172

                                                                Responds fast!
                                                                avg. 1 hour 21 minutes

                                                                Price per night from

                                                                $172

                                                                Distance approx 8.68 km from Keswick

                                                                  10

                                                                  1 hr from TO - Cottage getaway on south shore Lake

                                                                  Ontario / Georgina

                                                                  Georgina house

                                                                  4 8 min stay varies

                                                                  • 4 bedrooms
                                                                  • sleeps 8
                                                                  • min stay varies
                                                                  • Child Friendly
                                                                  • Private garden

                                                                  Price per night from

                                                                  $292

                                                                  Price per night from

                                                                  $292

                                                                  Distance approx 19.88 km from Keswick

                                                                    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 16.21 km from Keswick

                                                                    (5) Excellent 

                                                                    Certificate of Excellence

                                                                      26

                                                                      Country Cabin on Farm Near Newmarket Toronto

                                                                      Ontario / Schomberg

                                                                      Schomberg guest house

                                                                      1 6 1 night min

                                                                      • 1 bedroom
                                                                      • sleeps 6
                                                                      • 1 night min
                                                                      • Nearest beach 44 mi
                                                                      • Child Friendly
                                                                      • Air conditioning

                                                                      Certificate of Excellence

                                                                      Price per night from

                                                                      $99

                                                                      Price per night from

                                                                      $99

                                                                      Distance approx 11.3 km from Keswick

                                                                      (9) Average 

                                                                        25

                                                                        Beautiful cottage in 50 acres of land near Lake Simcoe

                                                                        Ontario / Uxbridge

                                                                        Uxbridge house

                                                                        6 12 3 nights min

                                                                        • 6 bedrooms
                                                                        • sleeps 12
                                                                        • 3 nights min
                                                                        • Beach / lakeside relaxation
                                                                        • Nearest beach 24 mi
                                                                        • Child Friendly
                                                                        “Great weekend” I came up with my friends for the weekend to celebrate my birthday, I was a little nervous because I didn't know what to expect because I've never done anything like this but it turned out to be a great weekend. The place is big and not

                                                                        Price per night from

                                                                        $257

                                                                        Price per night from

                                                                        $257

                                                                        Distance approx 6.4 km from Keswick Show on Map

                                                                          6

                                                                          Lake Simcoe's Sutton Beauty, 4 BR, 10 Min 404, 1 Min To Lake, Year Round

                                                                          Ontario / Georgina

                                                                          Georgina house

                                                                          4 14 1 night min

                                                                          • 4 bedrooms
                                                                          • sleeps 14
                                                                          • 1 night min
                                                                          • Child Friendly
                                                                          • Air conditioning
                                                                          • Pet Friendly

                                                                          Price per night from

                                                                          $270

                                                                          Price per night from

                                                                          $270

                                                                          Distance approx 12.27 km from Keswick

                                                                            12

                                                                            The perfect little getaway!

                                                                            Ontario / Georgina

                                                                            Georgina bungalow

                                                                            1 2 2 nights min

                                                                            • 1 bedroom
                                                                            • sleeps 2
                                                                            • 2 nights min
                                                                            • Nearest beach 15 mi

                                                                            Price per night from

                                                                            $94

                                                                            Price per night from

                                                                            $94

                                                                            Distance approx 16.21 km from Keswick

                                                                              7

                                                                              Holiday Christmas Event Hosting Space in Country

                                                                              Ontario / Schomberg

                                                                              Schomberg house

                                                                              1 40 1 night min

                                                                              • 1 bedroom
                                                                              • sleeps 40
                                                                              • 1 night min
                                                                              • Child Friendly

                                                                              Price per night from

                                                                              $258

                                                                              Price per night from

                                                                              $258