
Holiday houses in Simcoe County
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Top-rated holiday rentals in Simcoe County
Guests agree: these stays are highly rated for location, cleanliness and more.
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Popular amenities for Simcoe County holiday rentals
Other great holiday rentals in Simcoe County
Top Guest favourite

Home in Georgian Bay
4.99 out of 5 average rating, 90 reviewsA-Frame in the Woods of GeorgianBay, Muskoka
Superhost

Cottage in Victoria Harbour
5 out of 5 average rating, 3 reviews3 Bdrm Beachfront Oasis-Sunsets!
Top Guest favourite

Cabin in Shelburne
5 out of 5 average rating, 39 reviewsMaple Lane Log Cabin, in Mono.
Top Guest favourite

Cottage in Orillia
5 out of 5 average rating, 30 reviewsLuxury lakefront cottage escape
Guest favourite

Cottage in Sebright
4.98 out of 5 average rating, 43 reviewsTranquil Private Lakefront Cottage Haven
Top Guest favourite

Tiny home in East Gwillimbury
5 out of 5 average rating, 15 reviewsTiny Home Farm Stay
Top Guest favourite

Home in Barrie
4.98 out of 5 average rating, 63 reviewsBright basement apt with private entrance, Barrie
Guest favourite

Cottage in Innisfil
4.92 out of 5 average rating, 39 reviewsLakefront Luxury with Private Dock
Destinations to explore
- Rentals with a hot tub Simcoe County
- Cabin rentals Simcoe County
- Bed and breakfasts Simcoe County
- Fitness-friendly rentals Simcoe County
- Rentals with beach access Simcoe County
- Private suite rentals Simcoe County
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- Rentals with pools Simcoe County
- Boutique hotel rentals Simcoe County
- Rentals with an EV charger Simcoe County
- House rentals Simcoe County
- Rentals with breakfast Simcoe County
- Chalet rentals Simcoe County
- Waterfront rentals Simcoe County
- Rentals with a kayak Simcoe County
- Guesthouse rentals Simcoe County
- Rentals with outdoor seating Simcoe County
- Ski-in/ski-out rentals Simcoe County
- Rentals with a fireplace Simcoe County
- Smoking-friendly rentals Simcoe County
- Townhouse rentals Simcoe County
- Tiny house rentals Simcoe County
- Villa rentals Simcoe County
- Rentals with a sauna Simcoe County
- Family-friendly rentals Simcoe County
- Apartment rentals Simcoe County
- Kid-friendly rentals Simcoe County
- Rentals with a fire pit Simcoe County
- Beachfront rentals Simcoe County
- Rentals with a washing machine and dryer Simcoe County
- Farmstay rentals Simcoe County
- Condo rentals Simcoe County
- Rentals with lake access Simcoe County
- Rentals with a patio Simcoe County
- Bungalow rentals Simcoe County
- Cottage rentals Simcoe County
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- Pet-friendly rentals Simcoe County
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- Blue Mountain Village
- TPC Toronto at Osprey Valley
- Port Carling Golf & Country Club
- Horseshoe Resort
- Osler Bluff Ski Club
- Angus Glen Golf Club
- Beaver Valley Ski Club
- Devil's Glen Country Club
- Muskoka Lakes Golf and Country Club
- Lake Joseph Golf Club
- Georgian Bay Islands National Park
- Craigleith Ski Club
- Dagmar Ski Resort
- Snow Valley Ski Resort
- Mount St. Louis Moonstone
- Hockley Valley Resort - Golf, Spa and Ski
- The Club At Bond Head
- Muskoka Bay Resort
- Wooden Sticks Golf Club
- Lakeridge Ski Resort
- Alpine Ski Club
- The Georgian Peaks Club
- Goodwood golf club
- Caledon Country Club