Holiday rentals in Windy Island

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Top-rated holiday rentals in Windy Island

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Guest favourite
A rustic log cabin is nestled among tall trees, showcasing a welcoming entrance with a wooden porch. The surrounding foliage features various shades of green, while a canoe and kayak are positioned on the side, hinting at nearby water activities.
Cottage in Seguin
4.76 out of 5 average rating, 154 reviews

Muskoka Clearwater Log Cabin & Sauna

Nestled on the tranquil Clear Lake system just north of Lake Joseph, this Muskoka Log Cabin, built in 1938 by RW Wilson, offers an extraordinary retreat. This rustic, southern-facing cabin features crystal-clear waters, historic tall pines, a wood-fired sauna, and a private dock for a rare & captivating experience. The cabin uniquely showcases heritage log construction and the rich recreational history of the Georgian Bay region. Security cameras monitor the parking area 24/7 for your safety.

Guest favourite
Home in Meaford
4.87 out of 5 average rating, 532 reviews

Beach House Hideaway by Post Office Motel *HOT TUB

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

Guest favourite
A spacious glamping dome is nestled among lush green trees, showcasing large windows and a triangular design. The entrance is framed by rustic outdoor seating, and soft lighting emanates from inside, creating an inviting atmosphere amidst the surrounding foliage.
Dome in Utopia
4.95 out of 5 average rating, 272 reviews

Off-grid Glamping Dome Nestled in the Woods

Welcome to our private campsite in Utopia, ON. Our family’s glamping dome is your chance to experience a unique getaway surrounded by the sights & sounds of nature. Amenities include camping essentials & some glamping perks: king size bed, bbq, fireplace, Indoor incineration toilet, soap & water, outdoor shower (summer only), kettle, cooking utensils. Nearby is Purple Hill Lavender Farms, Drysdale's Tree Farm, Tiffin Conservation Area, Nottawasaga & golf courses. Wasaga Beach is 30 min away.

Guest favourite
Tiny home in Rosseau
4.91 out of 5 average rating, 166 reviews

Treehouse + cedar sauna

Perched atop a dramatic cliff overlooking a private pond, this one-of-a-kind off-grid treehouse is surrounded by acres of untouched forest and rugged rock cliffs. Designed for total privacy and tranquility, it’s the perfect place to unplug, slow down, and reconnect with nature. Spend your days canoeing or simply soaking in the peaceful views. As night falls, gather around the bonfire to roast marshmallows, unwind in your private sauna, and enjoy breathtaking stargazing far from city lights.

Top guest favourite
The entrance of a yurt is featured, showcasing a wooden deck with a decorative orange door. The circular structure is surrounded by lush greenery, highlighting the natural setting. Soft light filters through the trees, creating a peaceful outdoor environment.
Yurt in Meaford
4.99 out of 5 average rating, 191 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.

Top guest favourite
A modern two-story house is framed by tall trees, set against a backdrop of warm sunset hues. A stone driveway leads to the entrance, which is adorned with welcoming plants and porch lighting, creating an inviting entryway into the home.
Cabin in Huntsville
5 out of 5 average rating, 164 reviews

Cozy Cabin with hot tub, Sauna, hot yoga studio.

Welcome to D’oro Point overlooking Mary lake. We invite you to come relax, restore, and reconnect with nature on our 7.5 acres of wooded bliss. With only an approx 3 minute walk to our quaint neighbourhood beach, we are close enough to enjoy the lively lake life, yet maintain a private retreat feel. Stay on property and reap the health benefits of our private spa like amenities, which include the sauna, infrared hot yoga studio, and hot tub. Or, go out and explore all Muskoka has to offer.

Top guest favourite
A handcrafted timber frame cabin is set among trees, featuring natural wood siding and large windows that invite the outdoors in. A welcoming porch is accessed by a wooden staircase, while a covered area to the side provides shelter. The surrounding forest complements the rustic design.
Cabin in Bracebridge
5 out of 5 average rating, 274 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.

Superhost
The charming exterior of the bunkie features rustic wooden siding and three large windows. A welcoming front porch is furnished with two chairs and a small table, surrounded by a natural landscape of trees and open space, showcasing the tranquility of the setting.
Tiny home in Coldwater
4.81 out of 5 average rating, 111 reviews

Bunkie On The River

Welcome to our four season bunkie retreat on the river. Leave the world behind and seek comfort and peace at Riverside Ranch. Imagine starting your day reconnecting with nature amidst wooded walking trails. Along your walk you see geese swimming in the river, goats exploring the woods, and Highland cattle grazing in the pasture. Upon return, you open the door to the crackle & pop of a toasty wood burning sauna, followed by an icy cold plunge in the river. *No air-conditioning*

Top guest favourite
A secluded treehouse is nestled among tall trees, showcasing a modern design featuring large windows and a sloped roof. The structure is elevated, supported by solid timber, and surrounded by fallen leaves, highlighting the natural beauty of the forested setting.
Treehouse in Dorset
4.96 out of 5 average rating, 310 reviews

Raven's Roost- private luxury treehouse with sauna

Unplug your tech and let the sights and sounds of the forest be your muse. Treat your body to the healing powers of a eucalyptus sauna. Cool down in the outdoor shower, stargaze, crack a book, play some Scrabble, colour or write. Sing with the wolves, skate through the forest, canoe, climb, swim, ski or snowmobile from your door to the OFSC trail. The quaint town of Dorset is in the center of one if Canada's most impressive landscapes. Escape. Exhale.

Top guest favourite
Cabin in Huntsville
4.95 out of 5 average rating, 598 reviews

Aux Box Muskoka | Boutique | Private Nordic Spa

Escape to The Aux Box—a private boutique cabin nestled in the Muskoka woods with river views. Every amenity is exclusively yours, including the Nordic spa with a sauna, hot tub, cold plunge, and outdoor shower (summer). A short trail leads to your private dock with lounge chairs and canoe on the Muskoka River. Inside, enjoy custom cabinetry, a spa-inspired bathroom, and bespoke Canadian amenities, all just 10 minutes from downtown Huntsville.

Top guest favourite
A spacious cottage is set on a rocky landscape, surrounded by lush greenery. Multiple wooden decks and staircases connect the main entrance to the natural terrain. The structure features a welcoming exterior with a mix of wood accents and a shingled roof.
Cottage in MacTier
4.89 out of 5 average rating, 256 reviews

Eaglesnest 4 season, HOT TUB, SAUNA, Pickleball

"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 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

Top guest favourite
Cabin in Sprucedale
5 out of 5 average rating, 121 reviews

Black Fox Cabin with Private Nordic Spa

Welcome to your serene escape in our brand new cabin! Nestled in a very private pine forest on a 6-acre lot, our modern cabin offers a full spa-like experience designed for ultimate relaxation and connection with nature. This tranquil retreat features a cozy firepit, a modern sauna with panoramic views, cold plunge and a rejuvenating hot tub. Perfect after a day of exploring the beautiful surroundings.

Popular amenities for Windy Island holiday rentals

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  3. Ontario
  4. Parry Sound District
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