Cottage Rentals in Lake Simcoe - Simcoe County

$1,000 CAD
Per Night

An 8 bedroom lakefront home perfect for family gatherings.
Cottage Rental in Barrie, Canada
8 Bedrooms · 14 Guests · #298512

$275 CAD
Per Night

Ye Old Country Store Inn close to two cities, lakes, biking trails and ski resorts
Vacation Rental in Oro Medonte, Canada
3 Bedrooms · 10 Guests · #361994

$143 CAD
Per Night

Cute And Cozy Cottage On Lake Simcoe In Orillia
Cottage Rental in Orillia, Canada
3 Bedrooms · 6 Guests · #286650

$200 CAD
Per Night

Lake Simcoe - 4 Season Lake House
Vacation Rental in Jacksons Point, Canada
3 Bedrooms · 6 Guests · #337912

$650 CAD
Per Night

Waterfront Executive Cottage
Vacation Rental in Shanty Bay, Canada
5 Bedrooms · 12 Guests · #325032

$275 CAD
Per Night

Horseshoe Valley Fieldview Farm
Vacation Rental in Coldwater, Canada
5 Bedrooms · 12 Guests · #292405

$210 CAD
Per Night

Horseshoe Valley Farm
Vacation Rental in Coulson, Canada
3 Bedrooms · 10 Guests · #289633

$132 CAD
Per Night

Simcoe Lake House
Vacation Rental in Orillia, Canada
3 Bedrooms · 6 Guests · #299302

$430 CAD
Per Night

Sunset Paradise
Vacation Rental in Brechin, Canada
5 Bedrooms · 10 Guests · #299263

$365 CAD
Per Night

Heron's Landing - Georgina Island, Ontario
Cottage Rental in Georgina Island, Canada
3 Bedrooms · 10 Guests · #173983

$300 CAD
Per Night

Horseshoe Valley Chalet
Chalet Rental in Horseshoe Valley, Canada
4 Bedrooms · 10 Guests · #296635

$350 CAD
Per Night

Waterfront Cottage In Orillia
Cottage Rental in Orillia, Canada
1 Bedroom · 2 Guests · #262443

$421 CAD
Per Night

Upscale Beachfront On Lake Couchiching
Cottage Rental in Orillia, Canada
2 Bedrooms · 10 Guests · #186346

$500 CAD
Per Night

Spacious Suites/Great Amenities - Oro-Medonte
Chalet Rental in Oro-medonte, Canada
2 Bedrooms · 8 Guests · #178998

$180 CAD
Per Night

Whispering Pines B&B - Jackson's Point, Ontario
Bed & Breakfast Rental in Jackson's Point, Canada
1 Bedroom · 2 Guests · #174643

$450 CAD
Per Night

Grove Pl Big Bay Point Lake Simcoe - Ontario
Cottage Rental in Innisfil, Canada
3 Bedrooms · 10 Guests · #171150

$286 CAD
Per Night

Christie's Log Home - 1057
Cottage Rental in Lake Simcoe, Canada
4 Bedrooms · 8 Guests · #361306

$371 CAD
Per Night

Big Bay Point - 962
Cottage Rental in Lake Simcoe, Canada
4 Bedrooms · 8 Guests · #243428

$171 CAD
Per Night

Lakeview - 959
Cottage Rental in Lake Simcoe, Canada
5 Bedrooms · 10 Guests · #242855

$229 CAD
Per Night

Redwood - 828
Cottage Rental in Rama, Canada
3 Bedrooms · 8 Guests · #229356

$114 CAD
Per Night

Grove Place - 820
Cottage Rental in Innisfil, Canada
3 Bedrooms · 8 Guests · #229351

$145 CAD
Per Night

Gypsy By The Lake Bed & Breakfast
Vacation Rental in Jackson's Point, Canada
2 Bedrooms · 6 Guests · #178897

$95 CAD
Per Night

== Holiday Week Dec 25 - Jan 1 == Luxury Ski-In-Ski-Out Resort 1 Hr From Toronto
Vacation Rental in Collingwood, Canada
2 Bedrooms · 8 Guests · #369734

$300 CAD
Per Night

Luxury Chalet Rental on Lake Simcoe
Vacation Rental in Orillia, Canada
4 Bedrooms · 8 Guests · #370050

$95 CAD
Per Night

== Holiday Week Dec 23-30 == Luxury Ski-In-Ski-Out Resort 1 Hr From Toronto
Vacation Rental in Barrie, Canada
2 Bedrooms · 8 Guests · #369774

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Lake Simcoe - Simcoe County Vacation Rentals, Cottages & More!

Located in south central Ontario, Simcoe County cottage rentals are scattered along the shores of Georgian Bay and Lake Simcoe among picturesque meadows, marshes, and forests.

Lake Simcoe and Georgian Bay are two of Ontario’s top kitesurfing and windsurfing destinations and Wasaga Beach, which, at 14 kilometres long, is the longest freshwater beach in the world, is a swimming and sunbathing paradise. Anglers will be well served with catches of bass, pike, and walleye and with over 50 golf courses, there is no shortage of opportunities for visitors to hit the links. 

At the region’s national and provincial parks, popular activities include hiking, cycling, mountain biking, and horseback riding in the summer, and cross-country skiing, snowshoeing, and snowmobiling come winter. Further, nearby Blue Mountain provides Ontario’s best downhill skiing and snowboarding and a range of après-ski activities for adults and kids.

With plenty of restaurants, cafés, pubs, and spas in the region, there’s no shortage of places to retire to after a day on the water, trails, or slopes. Sample a hoppy beer or two at Flying Monkey Craft Brewery, or take a drive along the Apple Pie Trail, a scenic route that stops at orchards, vineyards, and eateries. 

Just 90 minutes north of Toronto, Simcoe County is a very popular place to rent a cottage in Ontario.

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