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, 443 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

Guest favourite

Cottage in Parry Sound

4.93 out of 5 average rating, 111 reviews

☀ Private Waterfront LogStyle Cottage w/ Lakeview!

Complete Privacy and Serenity Within 2-Hour Drive From The Greater Toronto Area (GTA). This One-of-a-Kind Dog Friendly Cottage Amasses Private Shoreline Direct Access to The Lake With A Sandy Beach & Open Lake View From The House! Great outdoor space perfect to explore & play! Smart TV (FireTV), wireless internet (Wi-Fi), children friendly, books & table games, coffee & tea, fully equipped kitchen with appliances, dishwares & utenstils. Outdoor - Canoe, BBQ grill, Outdoor tables & chairs, etc.

Guest favourite

Cottage in Tiny

4.97 out of 5 average rating, 129 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, 153 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

4.95 out of 5 average rating, 264 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.

Guest favourite

Home in Georgian Bay

4.97 out of 5 average rating, 106 reviews

A-Frame in the Woods of GeorgianBay, Muskoka

Welcome to our A-frame in the heart of Georgian Bay, Ontario! Perfect for family escapes and relaxing couples weekends in Muskoka. This cozy retreat has three bedrooms and accommodates up to six guests. With Six Mile Lake and Whites Bay just a stroll away, indulge in serene swims or explore the local golfing, breweries, and skiing at Mount St. Louis. Immerse yourself in nature's embrace while relishing the comforts of our picturesque A-Frame home—a perfect family getaway for every season!

Top Guest favourite

Cabin in Bracebridge

5 out of 5 average rating, 204 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

Guesthouse in Parry Sound

4.91 out of 5 average rating, 148 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! 🍂

Guest favourite

Treehouse in Utterson

4.96 out of 5 average rating, 223 reviews

The Water’s Edge * * Unique Muskoka Treehouse * *

CottageCreators presents a once-in-a-lifetime (or as often as you’d like!) Muskoka escape. Perched among the treetops on one of the region’s most stunning lakes, this rustic-luxury retreat offers a floating hammock net, two-sided indoor/outdoor fireplace, and private dock for swimming, canoeing, kayaking and SUP. Fall asleep to the gentle sounds of the lake, wake up to sunrise through the trees, and unwind in total seclusion—just you, the forest, and the water.

Top Guest favourite

Cabin in Huntsville

4.95 out of 5 average rating, 541 reviews

Aux Box Muskoka | Boutique | Sauna | Hot Tub

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

Condo in Parry Sound

4.9 out of 5 average rating, 124 reviews

Discover beautiful Parry Sound

Beautifully renovated, coxy, spacious 3 bedroom apartment in downtown Parry Sound with views of historic Trestle Bridge. Steps to shops, waterfront trail, restaurants, the new Trestle Brewery and Pub, and Legend Distillery. It's walking distance to the hospital. Snowmobile trails on the doorstep. Private parking for two, vehicles. The apartment is located on the second floor of our duplex. Parry Sound is located in a UNESCO Biosphere reserve.

Guest favourite

Cottage in Tiny

4.94 out of 5 average rating, 299 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. License #STRTT-2025-008