Holiday houses in Windy Island

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Top-rated holiday rentals in Windy Island

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Guest favourite

Home in Meaford

4.87 out of 5 average rating, 418 reviews

Waterfront* Hot Tub* - Beachhouse Hideaway *Unique

This beach house was designed with relaxation and the enjoyment of togetherness in mind. Let your worries melt away as you slip into the warmth of this water side hot tub featuring stunning view across Georgian Bay and up the mountain side, as fresh snow falls around you. The open concept design makes this the perfect place to gather with family and friends w/ walkout waterfront patio and dock access for swimming. 2 min to downtown Meaford, 20 min to Blue Mtn, 1.5 hrs to Tobermory. Hiking Trails

Superhost

Cottage in MacTier

4.91 out of 5 average rating, 110 reviews

Baysong Cottage, Hot Tub and Sauna on Georgian Bay

*Winter All Wheel Drive and Winter Tires Required* Welcome to Baysong Cottage. We are right on the water, with a big dock, sauna and hot tub all yours to enjoy. This is the perfect getaway winter and summer. Enjoy our dock for swimming and boating, our sauna and hot tub for a rejuvenating spa experience, and all day south west facing sunshine. Great for boating, fishing, sailing, swimming, snowmobiling, ice fishing or just a getaway to enjoy a campfire, some board games and some time together.

Guest favourite

Cottage in Meaford

4.93 out of 5 average rating, 178 reviews

Cosy and modern cottage on beautiful Georgian Bay

Enjoy panoramic views of Georgian Bay from this charming modern cottage on Paynter's Bay. Only eight minutes from Owen Sound, our cottage also borders on the quiet and beautiful Hibou Conservation Area where you can enjoy birding, hikes in forest and shoreline, and a great sandy beach and modern playground for the kids. Cuddle up next to the gorgeous modern Morso woodstove. Adventure awaits you with lots of skiing, biking, snowmobiling and the waterfall wonders of the Niagara Escarpment nearby.

Guest favourite

Cottage in Tiny

4.97 out of 5 average rating, 112 reviews

Ultimate Georgian Bay Vacation Getaway

Come and stay at our beautifully renovated *all-season* beachfront cottage and enjoy a breathtaking panoramic view of Georgian Bay! You'll discover the cottage sitting atop a sand dune, right on one of the most stunning freshwater beaches in the world. This rare location hosts a private covered deck hovering over the white sand, in a beach house closer to the bay than anywhere else around! Summer guests also enjoy use of a heated salt water pool and large resort deck created by Paul Lafrance.

Top Guest favourite

Yurt in Meaford

4.99 out of 5 average rating, 123 reviews

Quiet Retreat for Two

Spend a starry night in the country with the comfort of a soft bed, a wood stove, and plenty of space both indoors and out. Our yurt is located in a pocket of trees next to rolling farm fields and beautiful conservation land that the Rocklyn creek meanders through. You can prepare your meals in a sweet outdoor kitchen that is entirely screened in- or choose to sit by the fire. Bruce Trail access is just around the corner, and the towns of Meaford and Owen Sound are a short scenic drive away.

Guest favourite

Barn in Parry Sound

4.94 out of 5 average rating, 234 reviews

KING SIZE BED Barn style loft apartment private

Very private apartment that you will have all to yourself that’s above a barn style garage. It has everything you need for a very comfortable stay. The perfect little getaway situated near 2 lakes with public beaches and boat launches with in a short 3 minute walking distance or even shorter drive. Parry sounds 7 minutes away. there’s Restaurants near by and there’s also a 24 hour convenient store/gas station near by! The locations very nice to relax and explore what the area has to offer.

Top Guest favourite

Cabin in Bracebridge

5 out of 5 average rating, 188 reviews

Secluded Lakeside Retreat - Atkins Hideaway

Tucked in the heart of Muskoka, this handcrafted timber frame cabin rests alongside a scenic spring-fed lake, surrounded by 8 acres of private forest. Only 10 minutes from Bracebridge, enjoy serene lake life and natural beauty while remaining close to town amenities, local shops, and eateries. Enjoy private dock relaxation, cozy cabin comforts, and outdoor fires. A Provincial Park Day Pass is included (*security deposit required) for added adventure. Come relax, recharge and reconnect.

Guest favourite

Cabin in Parry Sound

4.95 out of 5 average rating, 101 reviews

Bardo Cabins - Pine Cabin

One of Bardo Cabins' two, four-season sister-cabins; Pine Cabin is quietly nestled below a granite outcrop among towering old pines on the beautiful, quiet, fifteen acre Dube Lake. Hike, bike, snowshoe or ski the private two kilometers of trails, dive and sunbathe from your own floating dock or wade at a nearby sandy shore, relax bug-free on the screened-in porch listening to the sounds of Bardo's surrounding ten acres of mixed old growth forest, or venture beyond to nearby amenities.

Top Guest favourite

Cabin in Clarksburg

4.96 out of 5 average rating, 103 reviews

Tiny A-Frame near the Bruce Trail

Find yourself nestled among white pine trees just steps off the Bruce Trail! This tiny A-Frame is 100 sq.ft providing enough room for cozy comfort. The cabin is equipped with 2 stackable twin beds converting into a queen bed when desired. Our amenities contain all the essentials, including a BBQ, drinking and dish water, and an outhouse with a composting toilet. Centrally located to Old Baldy Lookout, Beaver Valley, Blue Mountain and Duncan Caves. The perfect spot to relax and unwind!

Guest favourite

Cottage in MacTier

4.87 out of 5 average rating, 202 reviews

“Eagles Nest” cottage with HOT TUB and SAUNA

"Eagles Nest", Twelve Mile Bay, Muskoka, on 4 Season Maintained Road & Access by Watercraft from Georgian Bay Breathtaking Views - Private and Quiet - Boating - Trophy Fishing - Huge Decks, Landings and Docks - Fire Pit (currently buried under all the snow we received.) 50' Dock takes up to 30' Boat - Excellent Swimming & Diving - Dock has Access Ladder Fish from Dock - Your Boat - Rent a Boat - Fishing Charter from our Dock - Snowmobile Route 21 Work remotely on our wifi

Guest favourite

Guesthouse in Utterson

4.93 out of 5 average rating, 166 reviews

Lakefront Muskokan Log Cabin

In the heart of Muskoka on 3 Mile Lake. This cozy Log Cabin is set on private property. This studio room has all modern amenities which include 65” Smart TV, Netflix, microwave, keurig coffee maker, mini-fridge, toaster-oven, hot plate, barbecue and wall mounted fireplace. It has two beds and a full bathroom with seated shower. The waterfront has a shallow entry or you can jump in from the dock. A canoe, 2 kayaks & life jackets are for your use. End your night with a campfire.

Guest favourite

Cabin in Baysville

4.98 out of 5 average rating, 131 reviews

Luxury cabin on private 60 acre forest in Muskoka

Disconnect and reconnect in nature at this unforgettable luxury off-grid cabin escape. The vibe is modern simplicity, with everything you need to truly relax in nature. Luxurious linens, kitchen essentials, and a curated selection of books invite you for a slow stay. The cabin runs on solar panels and is designed to stay warm in winter and cool in summer. Although there is wifi, we hope you forgo using it for stargazing at night or cozying up in front of the wood stove.