Jayne's Cottages

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Explore our exclusive Premium cottage and vacation home rentals.

Alternate pricing options are available for some properties. Keep an eye out for clickable prices to see the other options!

Windsong Point

Location: Cottage in Gravenhurst

From C$18,700 /Week
    ( plus taxes and fees )

    WINDSONG POINT AREA Located on a magnificent point on South Lake Muskoka! 10 minutes to Gravenhurst, 20 minutes to Bala, and 25 minutes to Bracebridge with 2 marinas close by. Enjoy boating or swimming in Lake Muskoka or shopping in the nearby towns. Just over 2 hours to Toronto - as close as it gets! PROPERTY WINDSONG POINT is located on an unparalleled property with 2 acres of land and…...

    Breathtaking cottage set right on the water's edge on Muskoka! Spacious, open concept living area with large windows exposing beautiful lakes views from all angles of the point. Front and back deck totalling 1500'. Bathroom for each bedroom! Hot tub!

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    Windsong Point

    WINDSONG POINT AREA Located on a magnificent point on South Lake Muskoka! 10 minutes to Gravenhurst, 20 minutes to Bala, and 25 minutes to Bracebridge with 2 marinas close by. Enjoy boating or swimming in Lake Muskoka or shopping in the nearby towns. Just over 2 hours to Toronto - as close as it gets! PROPERTY WINDSONG POINT is located on an unparalleled property with 2 acres of land and…

    Bedrooms 6
    Bathrooms 6
    # of Guests 14
    Pet Friendly? Yes

    Holiday Headquarters

    Location: Cottage in Port Severn

    • Booked July/August
    From C$18,700 /Week
      ( plus taxes and fees )

      HOLIDAY HEADQUARTERS AREA Located on Six Mile Lake in Georgian Bay Township within the District Municipality of Muskoka. Six Mile Lake is abundant with fishing and the deep waters are perfect for all water activities. Only a 1.5 hr drive from Pearson Airport and 15 minutes from Port Severn for essentials. 20 minutes from picturesque Honey Harbour on Georgian Bay. 35 minutes to Port Carling and other Muskoka attractions. For…...

      Spacious 10 bedroom, 7 bathroom cottage on Six Mile Lake! East exposure and large, level property! Privacy on dock or sandy beach!

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      Holiday Headquarters

      HOLIDAY HEADQUARTERS AREA Located on Six Mile Lake in Georgian Bay Township within the District Municipality of Muskoka. Six Mile Lake is abundant with fishing and the deep waters are perfect for all water activities. Only a 1.5 hr drive from Pearson Airport and 15 minutes from Port Severn for essentials. 20 minutes from picturesque Honey Harbour on Georgian Bay. 35 minutes to Port Carling and other Muskoka attractions. For…

      Bedrooms 10
      Bathrooms 7
      # of Guests 22
      Pet Friendly? Yes

      Bella Muskoka

      Location: Cottage in Port Carling

      • Booked July/August
      From C$18,000 /Week
        ( plus taxes and fees )

        BELLA MUSKOKA AREA Bella Muskoka cottage is located in close proximity to Port Carling (5 min), Windermere (12 min), and Bracebridge (18 min). Located in Scarcliffe Bay, on the eastern side of Lake Muskoka, just a little past the Millionaires Row shoreline of Lake Muskoka. Nice access across the lake to Walker's Point or through the Indian River to Port Carling. PROPERTY BELLA MUSKOKA is a new build! Walk into…...

        Elegant living at its finest in this brand new Bella of a cottage! 4 bdrm main cottage and 3 bdrm fully-contained Bunkie. 2 bdrms with ensuites. 5 Bathrooms! Wall of windows with southwest views of Lake Muskoka. Muskoka Room! Near Beaumaris!

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        • 4.5

        Bella Muskoka

        BELLA MUSKOKA AREA Bella Muskoka cottage is located in close proximity to Port Carling (5 min), Windermere (12 min), and Bracebridge (18 min). Located in Scarcliffe Bay, on the eastern side of Lake Muskoka, just a little past the Millionaires Row shoreline of Lake Muskoka. Nice access across the lake to Walker's Point or through the Indian River to Port Carling. PROPERTY BELLA MUSKOKA is a new build! Walk into…

        Bedrooms 7
        Bathrooms 4.5
        # of Guests 14
        Pet Friendly? Yes

        Strawberry Lane

        Location: Cottage in Bracebridge

        From C$5,000 - C$17,820 /Week
        • C$17,820 (Peak)
        • $10,000 /Holiday / March Break Week
        • $4,700 /
        • $5,000 /Off Season Week
        ( plus taxes and fees )

        STRAWBERRY LANE AREA Strawberry Lane is a cottage located on Strawberry Bay in Bracebridge, Ontario. This cottage offers total privacy, and easy access to amenities. Just a 12-minute drive from the heart of Bracebridge, guests can stock up on supplies or explore local shops and attractions without the hassle of a long drive. PROPERTY STRAWBERRY LANE offers guests ample parking space upon arrival, as well as peace and privacy, courtesy…...

        A truly elegant 6 bdrm cottage, with 5 full bathrooms and all-day sun. This breathtaking vacation home will leave guests wanting for nothing, with 220' of waterfront, complete privacy - a perfect blend of luxury and charm!

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        Strawberry Lane

        STRAWBERRY LANE AREA Strawberry Lane is a cottage located on Strawberry Bay in Bracebridge, Ontario. This cottage offers total privacy, and easy access to amenities. Just a 12-minute drive from the heart of Bracebridge, guests can stock up on supplies or explore local shops and attractions without the hassle of a long drive. PROPERTY STRAWBERRY LANE offers guests ample parking space upon arrival, as well as peace and privacy, courtesy…

        Bedrooms 6
        Bathrooms 5
        # of Guests 12
        Pet Friendly? Yes

        Maple Grove Manor

        Location: Cottage in Innisfil

        From C$18,000 /Week
          ( plus taxes and fees )

          MAPLE GROVE MANOR AREA This lovely home is situated on Lake Simcoe, in the rural neighborhood of Innisfil. Enjoy your morning Starbucks at Friday Harbour just a short drive away and 12 minute walk away. This lovely location is within 15 minutes to all the amenities in Barrie; shopping and dining, and is under an hour from Toronto. This property offers the best of cottage living close to the city!…...

          Enjoy this beautiful 4 bedroom, 4 bath, newer build, high end home on Lake Simcoe. Beautiful lake views! Muskoka Room and hot tub! Enjoy cottage life, in under an hour to Toronto with easy access in all four seasons!

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          Maple Grove Manor

          MAPLE GROVE MANOR AREA This lovely home is situated on Lake Simcoe, in the rural neighborhood of Innisfil. Enjoy your morning Starbucks at Friday Harbour just a short drive away and 12 minute walk away. This lovely location is within 15 minutes to all the amenities in Barrie; shopping and dining, and is under an hour from Toronto. This property offers the best of cottage living close to the city!…

          Bedrooms 4
          Bathrooms 4
          # of Guests 8
          Pet Friendly? Yes

          Belleview

          Location: Cottage in Rosseau

          From C$7,198 - C$13,000 /Week
          • C$13,000 (Peak)
          • $31,491 /Off Season Month
          • $7,198 /Off Season Week
          ( plus taxes and fees )

          BELLEVIEW AREA Located on the Little Lake Joe, Belleview offers amazing proximity to local hubs while maintaining its own privacy! Whether you want to visit the Rosseau Farmers Market, a waterski show at Clevelands House or enjoy shopping and the restaurants in Port Carling, these amenities are only a 14, 15 and 28 minute drive respectively! PROPERTY BELLEVIEW offers two separate cottages that are perched atop a gentle slope, providing…...

          Come experience this stunning cottage on Little Lake Joe! With plenty of water activities, a quaint interior, these amazing two cottages along with the beautiful views and property will make you feel at home.

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          Belleview

          BELLEVIEW AREA Located on the Little Lake Joe, Belleview offers amazing proximity to local hubs while maintaining its own privacy! Whether you want to visit the Rosseau Farmers Market, a waterski show at Clevelands House or enjoy shopping and the restaurants in Port Carling, these amenities are only a 14, 15 and 28 minute drive respectively! PROPERTY BELLEVIEW offers two separate cottages that are perched atop a gentle slope, providing…

          Bedrooms 5
          Bathrooms 3
          # of Guests 12
          Pet Friendly? Yes
          THREE MILE LAKE
          SUMMER SPECIAL: $32k/2 weeks & $45k/3 weeks

          El Dorado

          Location: Cottage in Nipissing South (Utterson)

          From C$8,046 - C$17,750 /Week
          • C$17,750 (Peak)
          • $15,000 /Holiday / March Break Week
          • $8,046 /Off Season Week
          • $5,500 /Off Season Weekend
          ( plus taxes and fees )

          EL DORADO AREA El Dorado is situated with south east exposure on the north end of Three Mile Lake. With minimal boat traffic in the surrounding bay, El Dorado offers a very calming and serene atmosphere. PROPERTY EL DORADO is perched atop a beautiful Muskoka landscape, amongst the trees, and overlooks the surrounding bay. This beautiful property has 280ft of frontage and provides renters with both comfort and privacy! The…...

          Situated on Three Mile Lake, El Dorado is a stunning cottage that provides renters with an amazing Muskoka experience! With a beautifully finished interior, open-concept design and no detail overlooked, El Dorado is sure to be your dream getaway!

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          El Dorado

          EL DORADO AREA El Dorado is situated with south east exposure on the north end of Three Mile Lake. With minimal boat traffic in the surrounding bay, El Dorado offers a very calming and serene atmosphere. PROPERTY EL DORADO is perched atop a beautiful Muskoka landscape, amongst the trees, and overlooks the surrounding bay. This beautiful property has 280ft of frontage and provides renters with both comfort and privacy! The…

          Bedrooms 8
          Bathrooms 5
          # of Guests 18
          Pet Friendly? Yes

          Sandybeach Cottage

          Location: Cottage in Penetanguishene

          From C$17,600 /Week
            ( plus taxes and fees )

            SANDYBEACH COTTAGE AREA Located in Tiny Township on Georgian Bay, 20 minutes to Midland, 90 minutes to Toronto, and 1 hour to the Blue Mountains ski resort. PROPERTY SANDYBEACH COTTAGE - Beautiful private beach on level land and shallow entry into Georgian Bay. Circular driveway to cottage with double garage, lawn with kids play-structure and multiple seating areas including deck overlooking the lake. INTERIOR COTTAGE MAIN LEVEL KITCHEN High-end appliances,…...

            Large and welcoming beach house on the Tiny Beaches of Georgian Bay with privacy, a beautiful waterfront, clear water and stunning views!

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            Sandybeach Cottage

            SANDYBEACH COTTAGE AREA Located in Tiny Township on Georgian Bay, 20 minutes to Midland, 90 minutes to Toronto, and 1 hour to the Blue Mountains ski resort. PROPERTY SANDYBEACH COTTAGE - Beautiful private beach on level land and shallow entry into Georgian Bay. Circular driveway to cottage with double garage, lawn with kids play-structure and multiple seating areas including deck overlooking the lake. INTERIOR COTTAGE MAIN LEVEL KITCHEN High-end appliances,…

            Bedrooms 9
            Bathrooms 4
            # of Guests 16
            Pet Friendly? No

            Tiny Footprints in the Sand

            Location: Cottage in Tiny

            From C$17,600 /Week
              ( plus taxes and fees )

              TINY FOOTPRINTS IN THE SAND AREA Located in the heart of beach country, Tiny Footprints in the Sand is only 90 minutes north of Toronto! The world's longest freshwater beach, Wasaga Beach, is only 17 minutes away! A 22 minute drive will bring you to the town of Midland, where you can find all of your big-box stores as well as quaint downtown shops, cafés and restaurants that lead to…...

              Brand new state-of-the-art 3-Storey Beach House in Tiny! Jaw-dropping views of the magnificent blue waters of Georgian Bay await you at this four-season, luxury getaway with its bright southern exposure featuring incredible sunsets!

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              Tiny Footprints in the Sand

              TINY FOOTPRINTS IN THE SAND AREA Located in the heart of beach country, Tiny Footprints in the Sand is only 90 minutes north of Toronto! The world's longest freshwater beach, Wasaga Beach, is only 17 minutes away! A 22 minute drive will bring you to the town of Midland, where you can find all of your big-box stores as well as quaint downtown shops, cafés and restaurants that lead to…

              Bedrooms 4
              Bathrooms 5
              # of Guests 10
              Pet Friendly? Yes

              Chalet de Reve

              Location: Cottage in Peterborough South

              From C$17,500 /Week
                ( plus taxes and fees )

                CHALET DE REVE AREA Take a scenic drive through the countryside to Chemong Lake Just 1.5 hours from Pearson Airport and with year round accessibility! This property is conveniently located only 15 minutes from Peterborough! Chemong Lake is the largest lake in the Kawartha Chain of Lakes, covering more than 5,630 acres and offers countless hours of boating, fishing and water sports opportunities. Several golf courses are within a half…...

                Experience a dream come true at Chalet de Reve! This majestic 5 bedroom 5 bath post & beam cottage on Chemong Lake boasts luxury with high-end appliances, Restoration Hardware furniture throughout & a beautiful waterfront backyard for entertaining!

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                Chalet de Reve

                CHALET DE REVE AREA Take a scenic drive through the countryside to Chemong Lake Just 1.5 hours from Pearson Airport and with year round accessibility! This property is conveniently located only 15 minutes from Peterborough! Chemong Lake is the largest lake in the Kawartha Chain of Lakes, covering more than 5,630 acres and offers countless hours of boating, fishing and water sports opportunities. Several golf courses are within a half…

                Bedrooms 5
                Bathrooms 5
                # of Guests 10
                Pet Friendly? No

                Muskoka Bliss

                Location: Cottage in Muskoka Lakes

                • Booked July/August
                From C$17,000 /Week
                  ( plus taxes and fees )

                  MUSKOKA BLISS AREA Muskoka Bliss cottage is located 6 Minutes from Minett, 10 minutes from Port Sandfield, 12 minutes to the town of Rosseau. Northern exposure in open bay for beautiful all-day sun and sunrises and spectacular sunsets! PROPERTY MUSKOKA BLISS is a new luxury cottage with gorgeous views overlooking Lake Rosseau. Natural gardens, lovely ground cover, and beautiful planters are strategically placed around the property. The details enhance the…...

                  Open up the outdoors! This absolutely beautiful brand-new cottage will give you a view like none other from any vantage point! Beautiful interior matches the gorgeous views for upscale luxury! 3 Bdrms each with own Bath! Kids Upper Bedroom sleeps 6!

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                  Muskoka Bliss

                  MUSKOKA BLISS AREA Muskoka Bliss cottage is located 6 Minutes from Minett, 10 minutes from Port Sandfield, 12 minutes to the town of Rosseau. Northern exposure in open bay for beautiful all-day sun and sunrises and spectacular sunsets! PROPERTY MUSKOKA BLISS is a new luxury cottage with gorgeous views overlooking Lake Rosseau. Natural gardens, lovely ground cover, and beautiful planters are strategically placed around the property. The details enhance the…

                  Bedrooms 4
                  Bathrooms 3
                  # of Guests 12
                  Pet Friendly? Yes

                  Havelock

                  Location: Cottage in Muskoka Lakes

                  From C$17,000 /Week
                    ( plus taxes and fees )

                    HAVELOCK AREA The Havelock cottage is located only 6 minutes from Minett, 10 minutes from Port Sandfield, 10 minutes to the town of Rosseau. SW exposure promises breathtaking sunsets! PROPERTY HAVELOCK is a beautifully appointed luxury cottage with 240 foot frontage overlooking Lake Rosseau! SW exposure, new dock (12x40), outside seating! Amazing property in desirable Muskoka location. INTERIOR The cottage is light and bright with very high quality finishes. There…...

                    Beautifully decorated, 5 bdrm, 4 bath cottage on Lake Rosseau! Come experience everything Muskoka has to offer. Separate wing with own primary + ensuite, SW exposure, firepit, 240 frontage, dining room table seats 10! Amazing views! New dock!

                    Book Now
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                    Havelock

                    HAVELOCK AREA The Havelock cottage is located only 6 minutes from Minett, 10 minutes from Port Sandfield, 10 minutes to the town of Rosseau. SW exposure promises breathtaking sunsets! PROPERTY HAVELOCK is a beautifully appointed luxury cottage with 240 foot frontage overlooking Lake Rosseau! SW exposure, new dock (12x40), outside seating! Amazing property in desirable Muskoka location. INTERIOR The cottage is light and bright with very high quality finishes. There…

                    Bedrooms 5
                    Bathrooms 4
                    # of Guests 10
                    Pet Friendly? Yes
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