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Vacation rentals in Windy Island

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Top-rated vacation rentals in Windy Island

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

Superhost
Home in Huntsville
Modern Waterfront Retreat in Muskoka
Experience modern waterfront living. Located on the Muskoka River, you are a short boat ride to the large Mary Lake or take the locks right into Huntsville. Minutes from downtown Huntsville which features great shopping and restaurants. In the summer, soak in up the sun on your private dock with a spot for your boat. Calm & clear water great for swimming is 30 steps from your front door. Enjoy the snow with skiing at Hidden Valley or check out a variety of winter activities at Arrowhead Park.
$346 per night
Superhost
Cottage in Waubaushene
Modern Chalet w/ Hot Tub on Trail - Ski/Hike/Run
Modern cottage with sunset views of Georgian Bay right on the paved Tay Shore Trail for running/biking/snowshoeing. Newly renovated from top to bottom! Enjoy the 500 sqft deck with year round Hot Tub, BBQ and patio table. Fire pit in the backyard. The house is on a large lot surrounded by evergreens for privacy. Across the trail you can access the water, 5 min walk to a sandy beach. 1.5hrs from Toronto, 30mins north of Barrie, 12mins to Mt St Louis Moonstone for skiing.
$129 per night
Superhost
Cottage in Bracebridge
The Hudson - Riverside Cabin, Bracebridge
Nestled in the pines on the Muskoka River is this cozy one-bedroom cottage, ideal for a couple’s retreat. The Hudson offers the best of all worlds: it is relaxing, tranquil, and private, but you’re only a 10-minute drive from the Town of Bracebridge with unique shops, restaurants, groceries, and breweries, not to mention numerous tourist attractions. Marked trails are direct across the river. For more photos and information visit us on IG (at) thehudson.riversidecabin
$139 per night

Other great vacation rentals in Windy Island

Superhost
Cabin in Washago
Black River Haus - Scandi Riverfront Cabin Muskoka
$173 per night
Superhost
Guesthouse in Collingwood
The Little House on the Creek
$163 per night
Superhost
Home in Bracebridge
Muskoka Hideaway-hot tub/private trails/wood stove
$179 per night
Superhost
Chalet in The Blue Mountains
Immaculate Blue Mountains chalet
$90 per night
Superhost
Apartment in Parry Sound
Crabtree House
$77 per night
Superhost
Condo in The Blue Mountains
Perfect Studio for 2 at the base of Blue!
$89 per night
Superhost
Apartment in Gravenhurst
Treetop Loft | Private Hot Tub + Spa | Muskoka Bay
$174 per night
Superhost
Condo in The Blue Mountains
Mountainside Studio Bliss: Just Renovated, Tennis
$93 per night
Superhost
Cottage in Huntsville
The Rock Lodge, At Mary Lake (+ Hot Tub)
$162 per night
Superhost
Chalet in The Blue Mountains
Blue Mountain / Collingwood Hill Side Condo
$94 per night
Superhost
Condo in The Blue Mountains
Hidden Haven - Shuttle to Blue Mountain Village
$86 per night
Superhost
Condo in The Blue Mountains
★Blue Mountain Village★ Cozy, Stylish, 360 Views
$152 per night

Destinations to explore

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