Holiday houses in Windy Island

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Top-rated holiday rentals in Windy Island

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Guest favourite
Cottage in Tiny
4.96 out of 5 average rating, 141 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
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, 141 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 sunlit living space features large windows with views of the lake, allowing natural light to fill the room. A cozy striped armchair and a simple wooden coffee table are positioned on a wooden floor. A round table with decorative placemats complements the inviting atmosphere.
Cottage in Parry Sound
4.93 out of 5 average rating, 163 reviews

Muskoka Waterfront w/ Hot tub (Silver Linings)

*No extra fees* Come enjoy our designer furnished, newly-built, 4-season, Silver Lining Muskoka Lakehouse. This cottage offers you and your loved ones the perfect getaway with tons to do and memories to make with Insta sunsets over a lake wrapping around the entire property, a sandy beach to dip your toes, hot tub to warm up with friends, fire pit for roasting marshmallows. Other amenities: fully stocked kitchen, treehouse, games, BBQ, 1 acre of privacy, pet bed, well maintained hot tub.

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, 239 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
The exterior of a barn-style loft is showcased, featuring a charming design with white vertical siding and a wooden double door. Large windows allow natural light to enter, while the surrounding landscape includes trees and autumn foliage, creating a serene atmosphere.
Barn in Parry Sound
4.95 out of 5 average rating, 291 reviews

KING SIZE BED Barn style loft apartment private

Very private loft apartment that you will have all to yourself 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 a short drive to 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.

Guest favourite
Guesthouse in Parry Sound
4.91 out of 5 average rating, 155 reviews

Parry Sound Bunkie |Dock, BBQ, Firepit & Pets

🍁 Escape to Hemlock Cabin, your private fall lakeside retreat. Wake to sunrise views over vibrant foliage, spend crisp autumn days kayaking, hiking, or enjoying the calm lake, then savor BBQ dinners on the covered patio. End evenings by the fire pit under starlit skies 🔥. With cozy interiors, A/C, and space for couples or small families, this rustic-meets-modern gem is perfect for leaf-peeping, relaxation, and making Muskoka memories. Book your fall getaway today! 🍂

Top Guest favourite
A modern cottage surrounded by snow-covered trees is depicted, showcasing large windows that reflect the colorful sunset. A circular hot tub and outdoor seating are visible on the patio, enhancing the tranquil and cozy ambiance of the property.
Cottage in Huntsville
5 out of 5 average rating, 132 reviews

Muskoka Spa & Golf Retreat with Sauna + Hot Tub

Embark on a family wellness journey at our Nordic farmhouse-style Cottage in Muskoka. Unwind in the wisteria-adorned hot tub or by the firepit, nestled in Muskoka chairs. This bungalow features airy ceilings, expansive windows, and a modern fireplace. While the en-suite offers a rejuvenating frameless shower and deep tub. The Muskoka river is 250m away, Port Sydney Beach a 10-min drive. Embrace year-round family fun and wellness. Your rejuvenating escape begins here.

Top Guest favourite
Cabin in Huntsville
4.95 out of 5 average rating, 557 reviews

Aux Box Muskoka | Boutique | Private Nordic Spa

Escape to the Aux Box, a boutique luxury cabin nestled in the Muskoka woods with serene river views. Designed for comfort and style, it features in-floor heating, custom cabinetry, and premium amenities. Step into your private Nordic Spa with a sauna, hot tub, and cold plunge for the ultimate relaxation. Enjoy total seclusion while being less than 10 minutes from the shops, dining, and charm of downtown Huntsville. A perfect blend of nature and luxury awaits.

Guest favourite
A warm living area features a stone fireplace as the focal point, with a cozy fire burning inside. Comfortable leather seating is arranged around a rustic wooden coffee table, complemented by small decorative items and soft textiles, while glass doors lead to another space.
Cottage in Tiny
4.93 out of 5 average rating, 319 reviews

Bluestone

Bluestone is located less than 10 minutes' drive from beautiful Awenda Provincial Park in Tiny, Ontario. Every choice was made with guest comfort in mind. In the Summertime, take a short walk down a wooded path to Georgian Bay and perfect swimming, or explore a hiking trail and take in the natural beauty of the area. In Winter, enjoy skiing and snowshoeing locally, or stay in, put a record on, and cozy up by the fire. Licence STRTT-2026-057

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
4.88 out of 5 average rating, 230 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
A serene pathway leads through lightly snow-covered trees to a geodesic dome illuminated by warm string lights. The dome's entrance, framed by the natural surroundings, invites guests into a cozy retreat amidst a tranquil winter landscape.
Dome in McKellar
4.97 out of 5 average rating, 119 reviews

Geodesic River Dome off grid 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 :)

Guest favourite
A wooden dock extends into calm water, featuring Adirondack chairs positioned for relaxation. Sunlight reflects off the water's surface, creating a serene atmosphere. Nearby, a small boat awaits at the bottom of the dock, framed by trees on the opposite shore.
Cottage in MacTier
4.92 out of 5 average rating, 121 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