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Vacation rental cottages in Orillia

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Top-rated cottages in Orillia

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

Lakefront Swim & Paddle on Lake Couchiching
Entire guest suite · 2 guests · 1 bed · 1 bath

Lakefront Swim & Paddle on Lake CouchichingCozy private rustic guest suite on beautiful waterfront property on Lake Couchiching (Muskoka S), featuring dock with spectacular sunset views, clear water for swimming (no weeds), use of kayak, canoe, BBQ, hammock and other outdoor amenities. Suite features private entrance, sliding doors to lake, double bed with new mattress, work desk and chair, 3-pc ensuite, small kitchenette, & cozy reading corner. Relaxing & friendly cottage life at its best! Just 115km from Toronto.

Trailside Retreat: Top Floor Suite
SUPERHOST
Entire rental unit · 4 guests · 2 beds · 1 bath

Trailside Retreat: Top Floor SuiteThe Trailside retreat is a modern apartment with large windows located directly across from Lake Couchiching and next to the Orillia trail system. Nestled amongst beautiful old trees the Trailside Retreat is the perfect spot to relax and enjoy a nice getaway! Across the road from a beautiful park and beach, 5 minutes from downtown Orillia, 15 minutes away from Horseshoe Resort, 20 Minutes away from Mt. St. Louis the Trailside retreat is a great all year round destination.

Lake Simcoe Waterfront Cottage Getaway
SUPERHOST
Entire residential home · 6 guests · 3 beds · 1.5 baths

Lake Simcoe Waterfront Cottage GetawayLake Simcoe Waterfront Cottage Getaway This is a great location for a couple, friends, or family looking to get away and relax. Lovely cozy home feel, with new appliances and central heating and air conditioning. The large deck has separate seating, dining areas, and offers a lovely view of the lake! The lakefront is available exclusively for your enjoyment. Sit on the dock and soak up some rays or enjoy a nightly star gaze. 1 canoe and 1 foam board are available for your use! (Pet Friendly!)

Vacation rentals for every style

Get the amount of space that is right for you.

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Popular cottage amenities in Orillia

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Houses in Orillia

SUPERHOST
  1. Entire guest suite
  2. Oro-Medonte
The Suite at Bass Lake Retreat
  1. Entire bungalow
  2. Orillia
Beautiful Waterfront Cottage - Boater's Paradise
  1. Entire cabin
  2. Orillia
Orkney Beach 1 on the shores of Lake Simcoe
  1. Entire rental unit
  2. Orillia
2-bedroom apartment located in downtown Orillia
SUPERHOST
  1. Entire rental unit
  2. Orillia
DaVel DeLuxe Relax apartment
  1. Entire rental unit
  2. Orillia
2 Bedroom Apartment - Steps away from Hospital
SUPERHOST
  1. Entire residential home
  2. Orillia
Mariposa Retreat Perfect for Family or Work
  1. Entire residential home
  2. Orillia
Lightfoot Trail Harbour home.
  1. Entire residential home
  2. Orillia
Orillia Getaway
SUPERHOST
  1. Entire cottage
  2. Orillia
Lakefront Tiny House
  1. Entire cottage
  2. Orillia
Cottage Retreat Near Lake Simcoe
  1. Entire guest suite
  2. Orillia
Crooked Dock Suite

Your guide to Orillia

Welcome to Orillia

The town of Orillia is a great base for exploring the Lake Simcoe region north of Toronto and all the outdoorsy activities that can be enjoyed there. Orillia is set on Lake Couchiching, which connects to the north end of Lake Simcoe, and the town’s beaches and parks are perched along the shore. For boaters, Lake Couchiching and Lake Simcoe are part of the historic Trent-Severn Waterway, connecting Lake Ontario with Georgian Bay. If you aren’t heading here with your own watercraft, local outfitters can rent you canoes, stand-up paddleboards, kayaks, and larger boats, and some offer lake cruises or fishing excursions. In town, the Orillia Museum of Art and History can introduce you to local culture, and you can learn more about a noted resident, the Canadian humorist Stephen Leacock, by touring his former home. You can also poke around the galleries and art studios of Orillia’s Peter Street Arts District downtown. From Orillia, head north to the Muskoka region — it’s a 30-minute drive to Gravenhurst — or explore the beaches and historic sites in the Midland area, 45 minutes to the northwest.


How do I get around Orillia?

Toronto’s Pearson International Airport (YYZ) is the major airport closest to the Lake Simcoe region, about an hour and 15 minutes by car from Orillia, depending on traffic. Public buses (with connections) or airport shuttles can take you between Orillia and Pearson Airport. Between downtown Toronto and Orillia, several buses a day travel in each direction. For drivers, traffic congestion can be particularly bad between Toronto and the Lake Simcoe region on summer and fall weekends, especially travelling northbound on Friday evenings and southbound on Sunday evenings. Within Orillia, Orillia Transit runs buses throughout the community. To travel elsewhere in the Lake Simcoe region, it’s easiest to get around with your own car. You can also explore by bike.


When is the best time to stay in a vacation rental in Orillia?

Orillia is a year-round community, but it really comes alive in the summer months when the weather is warm enough for activities in and around the lake. Since 1961, Orillia has hosted the summertime Mariposa Folk Festival, which has grown to include more than 100 music performances on several outdoor stages. The annual Streets Alive festival brings art outdoors every summer, too. Another good time to visit is during the fall foliage season, usually most vibrant in October. If you’re a skier or snowboarder, you can head for the ski hills in the Lake Simcoe region from December through March.


What are the top things to do in Orillia?

Stephen Leacock Museum

Canadian humorist Stephen Leacock (1869-1944) spent his summers by the lake in Orillia, where he built a stately home in 1928. His lakeside house is now a museum about his life and works, which include Sunshine Sketches of a Little Town, stories he published in 1912 about a fictional Ontario town that he likely modelled on Orillia.

Orillia Museum of Art & History

Located in Orillia’s Peter Street Arts District, the town’s culture and heritage museum has more than 10,000 artifacts from around the region. Although only a fraction are on view at any one time, the galleries also show temporary or travelling exhibitions.

Simcoe County Barn Quilt Trail

As you explore the Lake Simcoe region around Orillia, look for colorful barn quilts — quilt-inspired graphics painted on 4-by-8-foot aluminum panels and attached to barns around the area. There are more than 150 barn quilts in Simcoe County; you can find a map to guide your touring on the Tourism Simcoe County website.

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