Jacksons Point Rentals

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61 Houses

    10

    Rainbow-bow

    Georgina / Jacksons Point

    Jacksons Point cottage

    3 2 1 night min

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

    Price per night from

    $172

    Price per night from

    $172

    (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

        49

        Classy Homestyle Cottage (Lake Simcoe)

        Georgina / Jacksons Point

        Jacksons Point cottage

        4 13 1 night min

        • 4 bedrooms
        • sleeps 13
        • 1 night min
        • Child Friendly
        • Air conditioning
        • Pet Friendly

        Price per night from

        $165

        Price per night from

        $165

          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

          $91

          Price per night from

          $91

          Great rentals within 20 miles that match your search

          Distance approx 1.8 km from Jacksons Point

            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

            $271

            Responds fast!
            avg. 3 hours 23 minutes

            Price per night from

            $271

            Distance approx 8.35 km from Jacksons Point

            (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 8.37 km from Jacksons Point

                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 16.02 km from Jacksons Point

                (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 11.02 km from Jacksons Point

                    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 1.36 km from Jacksons Point

                      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 4.62 km from Jacksons Point

                      (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

                        Distance approx 13.65 km from Jacksons Point

                          10

                          3 Bedroom Furnished Apartment

                          Ontario / Barrie

                          Barrie apartment

                          3 5 14 nights min

                          • 3 bedrooms
                          • sleeps 5
                          • 14 nights min
                          • Child Friendly
                          • Car not necessary

                          Price per night from

                          $77

                          Responds fast!
                          avg. 2 hours 54 minutes

                          Price per night from

                          $77

                          Distance approx 13.16 km from Jacksons Point

                          (2) Excellent 

                            12

                            Renewed Resort Style Getaway Barrie w/ Pool!

                            Ontario / Barrie

                            Barrie house

                            3 8 min stay varies

                            • 3 bedrooms
                            • sleeps 8
                            • min stay varies
                            • Nearest beach 2 mi
                            • Swimming pool
                            • Child Friendly

                            Price per night from

                            $128

                            Responds fast!
                            avg. 2 hours 5 minutes

                            Price per night from

                            $128

                            Distance approx 17.79 km from Jacksons Point

                            (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 9.04 km from Jacksons Point

                              (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 8.68 km from Jacksons Point

                                (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
                                  …see more

                                  Price per night from

                                  $258

                                  Price per night from

                                  $258

                                  Distance approx 15.8 km from Jacksons Point

                                    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. 2 hours 8 minutes

                                    Price per night from

                                    $194

                                    Distance approx 9.19 km from Jacksons Point

                                      11

                                      SHABBY SHACK

                                      Ontario / Innisfil

                                      Innisfil beach hut

                                      1 2 2 nights min

                                      • 1 bedroom
                                      • sleeps 2
                                      • 2 nights min

                                      Price per night from

                                      $56

                                      Responds fast!
                                      avg. 1 hour 45 minutes

                                      Price per night from

                                      $56

                                      Distance approx 9.3 km from Jacksons Point

                                        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

                                        $516

                                        Responds fast!
                                        avg. 2 hours 33 minutes

                                        Price per night from

                                        $516

                                        Distance approx 0.1 km from Jacksons Point 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 2.73 km from Jacksons Point

                                            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 12.62 km from Jacksons Point

                                            (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 14.3 km from Jacksons Point

                                              (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

                                                $344

                                                Responds fast!
                                                avg. 1 hour 23 minutes

                                                Price per night from

                                                $344

                                                Distance approx 17.62 km from Jacksons Point

                                                (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 14.1 km from Jacksons Point

                                                    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 15.99 km from Jacksons Point

                                                      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 13.65 km from Jacksons Point

                                                      (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. 2 hours 54 minutes

                                                        Price per night from

                                                        $68

                                                        Distance approx 18.95 km from Jacksons Point

                                                          7

                                                          Manilla ChurchHouse

                                                          Ontario / Manilla

                                                          Manilla guest house

                                                          4 7 1 night min

                                                          • 4 bedrooms
                                                          • sleeps 7
                                                          • 1 night min
                                                          • Nearest beach 15 mi
                                                          • Pet Friendly

                                                          Price per night from

                                                          $237

                                                          Price per night from

                                                          $237

                                                          Distance approx 8.23 km from Jacksons Point

                                                            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

                                                            $214

                                                            Price per night from

                                                            $214

                                                            Distance approx 14.08 km from Jacksons Point

                                                              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 5.41 km from Jacksons Point

                                                                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 1.8 km from Jacksons Point

                                                                (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

                                                                  $429

                                                                  Price per night from

                                                                  $429

                                                                  Distance approx 10.38 km from Jacksons Point

                                                                  (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

                                                                    $737

                                                                    Price per night from

                                                                    $737

                                                                    Distance approx 19.63 km from Jacksons Point

                                                                      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

                                                                      Distance approx 17.77 km from Jacksons Point

                                                                        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 23 minutes

                                                                        Price per night from

                                                                        $35

                                                                        Distance approx 4.12 km from Jacksons Point

                                                                        (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

                                                                          $516

                                                                          Responds fast!
                                                                          avg. 1 hour 0 minutes

                                                                          Price per night from

                                                                          $516

                                                                          Distance approx 17.53 km from Jacksons Point

                                                                          (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 23 minutes

                                                                            Price per night from

                                                                            $86

                                                                            Distance approx 17.74 km from Jacksons Point

                                                                              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 23 minutes

                                                                              Price per night from

                                                                              $112