Holiday houses in Windy Island

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Top-rated holiday rentals in Windy Island

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Top Guest favourite
Treehouse in Huntsville
4.98 out of 5 average rating, 201 reviews

Magical TreeHouse I Hot Tub, Fireplace, Pets OK

Escape to our one-of-a-kind A-Frame TreeHouse, tucked among snowy Muskoka trees near Huntsville, ON. Slow down, cozy up, and enjoy winter’s beauty. Spend evenings by the fireplace, soak under the stars in the hot tub, or head out for adventure— skiing, snowshoeing, skating, and hiking are all close by. Highlights - Hot tub & fireplace - Snowshoes provided - Sweeping snowy forest views - Free Ontario Parks pass - 10-min walk to ski hill & lake 📷 See more @door25stays for photos & inspiration!

Top Guest favourite
A charming A-frame cabin is framed by lush trees, featuring a green metal roof and large windows that create a bright atmosphere. A wooden deck extends from the entrance, with a firepit surrounded by four Adirondack chairs positioned on a grassy area.
Cottage in Huntsville
4.98 out of 5 average rating, 392 reviews

Muskoka A-Frame + HOT TUB | Arrowhead | 4-Seasons

Welcome to Muskoka A-frame, the perfect couple’s getaway or solo retreat. Relax in the **NEW HOT TUB**. Wake up to swaying treetops, make gourmet meals & relax by the fire, with 2-story forest views. This classic 70’s A-frame cabin has been re-imagined for the modern world. Nest away or make it your base for 4-seasons of adventure. 3 min to a private beach. Hike, canoe or swim at Arrowhead or Limberlost Forest. And visit Huntsville for restaurants, breweries & local amenities just minutes away.

Guest favourite
A peaceful beach scene captures the soft sand shoreline leading to the water's edge. Gentle waves lap at the shore, and the sky is filled with warm sunset hues. A cottage is visible in the background, nestled among trees, enhancing the serene atmosphere.
Cottage in Tiny
4.96 out of 5 average rating, 135 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
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, 283 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
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, 223 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
A serene outdoor area is surrounded by tall trees, featuring two cabins with rustic exteriors. A fire pit made of stones is positioned centrally, with log seating arranged around it. A picnic table stands nearby, offering a communal space for gatherings.
Cabin in Kearney
4.95 out of 5 average rating, 583 reviews

Cozy Creek-Side Cabin

Small cabin in the woods with many seasonal uses. There is over 1000 adjoining acres of mixed forest & fields. Over 300 acres of privately owned land by the host plus over 700 acres of attached public crown lots accessible through private holdings, perfect for outdoor enthusiasts/nature lovers, as a launch pad into Algonquin Park, or as a quite retreat into the forest. Winter Activities and Uses Include: snowmobiling, ice fishing at a large selection of local lakes, snow shoeing etc.

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, 134 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 spa like amenities, which include the sauna, infrared yoga studio, and new hot tub. Or, go out and explore all Muskoka has to offer.

Top Guest favourite
A modern bathroom features a freestanding soaking tub situated next to a window, allowing natural light to fill the space. The vanity displays a mirror and toiletries. Nearby, a spacious bed with soft linens is visible, set against a backdrop of wooden walls.
Place to stay in Wasaga Beach
4.99 out of 5 average rating, 339 reviews

Newly Built Woodsy Retreat - Your Perfect Escape

Woodsy Loft, an ideal home base for not just the beach and stunning sunsets, but Blue Mtn, Scandinave Spa, C-wood, brand new casino, all close by. Many bars, restaurants, beach and other things to do, within 5 min. Great place to stay in, too. Packed with amenities like screened in patio, XL bathtub w/ towel warmer, King size bed, 'The Frame' TV, full kitchen, fast WIFI, motorized blind...and the list goes on. Situated and designed to offer max. privacy and relaxation.

Guest favourite
Guesthouse in Parry Sound
4.91 out of 5 average rating, 150 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
An aerial view showcases the modern cabin nestled among tall trees, featuring a large window that invites natural light. A hanging chair is visible on the porch, surrounded by lush greenery. Twinkling lights enhance the warm ambiance near the cabin's entrance.
Cabin in Huntsville
4.95 out of 5 average rating, 549 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
4.94 out of 5 average rating, 308 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

Top Guest favourite
The exterior of the cozy cabin showcases a rustic red facade with a welcoming front door. A small porch features two comfortable chairs and a blue lantern. Lush greenery and decorative stones provide a natural touch, creating a serene outdoor atmosphere.
Cabin in Burk's Falls
4.93 out of 5 average rating, 106 reviews

Little Red Cabin

When you step into our newly renovated cozy cabin we hope you feel the nostalgia of an old time rustic cottage but in a clean, new updated way. This cabin is the perfect little place for a romantic getaway or family adventure with everything you need for a relaxing home away from home experience. Located just minutes from Burks Falls and Highway 11 it’s a convenient place to call home while you explore the Almaguin Highlands and North Muskoka.

Popular amenities for Windy Island holiday rentals

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