
Holiday rentals 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

Flat in Innisfil
5 out of 5 average rating, 85 reviewsSpacious Apartment 5 Minute Walk to Innisfil Beach
Top guest favourite

Cabin in Orangeville
4.97 out of 5 average rating, 169 reviewsHockley Valley Cozy Cottage
Top guest favourite

Apartment in Innisfil
4.95 out of 5 average rating, 64 reviewsWalkout to Courtyard w/ Pool, Hot Tub and Fire Pit
Guest favourite

Guest house in Georgina
4.96 out of 5 average rating, 52 reviewsBright & Modern Lower Level Apt in Keswick
Guest favourite

Flat in Barrie
5 out of 5 average rating, 6 reviewsQueen Bed Suite-Private Entrance
Top guest favourite

Cottage in Innisfil
4.98 out of 5 average rating, 51 reviewsThe Gingerbread House | Near Lake + Wedding Venues
Superhost

Cottage in Innisfil
4.88 out of 5 average rating, 41 reviewsLakefront Luxury with Private Dock
Top guest favourite

Flat in Midland
5 out of 5 average rating, 43 reviewsHidden Gem
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- Blue Mountain Village
- Horseshoe Resort
- Snow Valley Ski Resort
- Port Carling Golf & Country Club
- Osler Bluff Ski Club
- Devil's Glen Country Club
- Craigleith Ski Club
- Angus Glen Golf Club
- Hockley Valley Resort - Golf, Spa and Ski
- Beaver Valley Ski Club
- Lakeridge Ski Resort
- Mount St. Louis Moonstone
- Lake Joseph Golf Club
- Wooden Sticks Golf Club
- The Club At Bond Head
- Muskoka Lakes Golf and Country Club
- The Georgian Peaks Club
- Caledon Country Club
- TPC Toronto at Osprey Valley
- Muskoka Bay Resort
- Georgian Bay Islands National Park
- Dagmar Ski Resort
- The Georgian Bay Club
- Windermere Golf & Country Club