Holiday rentals in Windy Island

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Top-rated holiday rentals in Windy Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost
Home in Meaford
4.87 out of 5 average rating, 525 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

Top guest favourite
The historic Beck House, a striking Victorian structure, stands with a distinctive red façade and slate roof. A spacious porch with white railings invites guests, while the well-kept lawn adds to its charm. A wooden sign identifies the property, blending history with a warm welcome.
Flat in Penetanguishene
4.9 out of 5 average rating, 535 reviews

The Haunted House Apt 302

As you pull into the driveway this 1885 Victorian towers above you, your mouth drops in awe of the size. Up the porch to enter a small front door, a dimly lit winding staircase creaks as you ascend to 3rd floor. Original architecture painted many times over oozes with history. 70 years ago the house was turned into apartments, unloved for many of those years, time has definately taken its tole, yet to the spirits within, their big old house still stands proud and distinguished in all its glory.

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, 270 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.

Top guest favourite
Tiny home in Rosseau
4.91 out of 5 average rating, 162 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, 188 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, 160 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, 268 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.

Top guest favourite
Dome in McKellar
4.95 out of 5 average rating, 148 reviews

Geodesic River Dome rustic remote super camping

Reconnect with nature and each other at this unforgettable river side escape. a stunning geodesic dome camping experience awaits you…sleep under the stars, enjoy a campfire overlooking the peaceful river, sip your morning coffee on your own private dock (seasonal), get ready to unplug and relax in all the best ways. Remember, you'll be super camping so expected camping things like bugs and an outhouse :), in the winter months it can be chilly, and in the summer can get hot.

Top guest favourite
Guest house in Parry Sound
4.96 out of 5 average rating, 330 reviews

Private Barn style loft king bed

Enjoy your own private loft retreat above a charming barn-style garage, thoughtfully equipped for a comfortable and relaxing stay. This cozy little getaway is just a short 3-minute walk or drive to two beautiful lakes with public beaches and boat launches, and only a quick 7-minute drive to Parry Sound for restaurants, shops, and local charm. A 24-hour convenience store and gas station are also nearby, making it the perfect peaceful spot to unwind and explore the area.

Top guest favourite
Cabin in Huntsville
4.95 out of 5 average rating, 590 reviews

Aux Box Muskoka | Boutique | Private Nordic Spa

Escape to The Aux Box — a private boutique cabin tucked into the Muskoka woods with river views and luxury at every turn. Unwind in your exclusive Nordic spa with a sauna, hot tub, cold plunge, and outdoor shower (summer). Inside, enjoy custom cabinetry, bespoke Canadian amenities, a kitchenette, and spa-like bathroom. Completely secluded, yet less than 10 minutes from downtown Huntsville. Coming soon: private waterfront access and canoe.

Top guest favourite
Cabin in Sprucedale
5 out of 5 average rating, 119 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.

Guest favourite
Cottage in MacTier
4.92 out of 5 average rating, 122 reviews

Baysong Cottage, with Sauna, on Georgian Bay

Welcome to Baysong Cottage. We are right on the water, with a big dock, canoe/kayaks and sauna all yours to enjoy. This is the perfect summer getaway. Enjoy our dock for swimming and boating, our sauna for a rejuvenating spa experience, and all day south west facing sunshine. Great for boating, fishing, sailing, swimming, or just a getaway to enjoy a campfire, some board games and some time together.

Popular amenities for Windy Island holiday rentals

  1. Airbnb
  2. Canada
  3. Ontario
  4. Parry Sound District
  5. Windy Island