
Guesthouse vacation rentals in Lake Simcoe
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouses in Lake Simcoe
Guests agree: these guesthouses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Lake Simcoe guesthouses
Family-friendly guesthouses

Cozy Private Ensuite Basement Bedroom

Parry Sound Bunkie |Dock, BBQ, Firepit & Pets

Luxury 1BD Suite/A+ Location!

Chic & Cozy 1Bed Guest Suite

Adorable, modern tiny home in Leslieville

Airport| Couples| Garden Suite| Skylight |Smart TV

Studio Blue, tiny home retreat

Cozy 2 Bedroom Guest Suite in Aurora
Guesthouses with a patio

Mono Countryside Home & Farm

Millcreek Riverfront Retreat Elora/Fergus

A Greyt Escape

Windfall Cottage On Little Lake

Warm rustic luxury chalet near lake & skiing

The Hideout

Private Guest House Retreat

Cozy Guesthouse Heart of RichmondHill Bayview
Guesthouse rentals with a washer and dryer

Country Cabin Escape | King Bed | Pet Friendly

Bright and Airy Guest Suite with Pool

Bright & Modern Lower Level Apt in Keswick

A bright & stylish urban studio

2BR cozy Apt close to dwtn, forests, hospital, hwy

Guesthouse Getaway

Hillside Studio: Georgian Bay + Small Town

Entire rental unit Richmond Hill
Destinations to explore
- Montreal Vacation rentals
- Greater Toronto and Hamilton Area Vacation rentals
- Greater Toronto Area Vacation rentals
- Mississauga Vacation rentals
- Niagara Falls Vacation rentals
- Pittsburgh Vacation rentals
- Grand River Vacation rentals
- St. Catharines Vacation rentals
- Northeast Ohio Vacation rentals
- Island of Montreal Vacation rentals
- Laurentides Vacation rentals
- Detroit Vacation rentals
- Rentals with a fireplace Lake Simcoe
- Smoking-friendly rentals Lake Simcoe
- Rentals with a washer and dryer Lake Simcoe
- Rentals with outdoor seating Lake Simcoe
- Rentals with breakfast Lake Simcoe
- Rentals with a firepit Lake Simcoe
- Pet-friendly rentals Lake Simcoe
- Rentals with an EV charger Lake Simcoe
- Family-friendly rentals Lake Simcoe
- Apartment rentals Lake Simcoe
- Rentals with lake access Lake Simcoe
- Rentals with beach access Lake Simcoe
- Condo rentals Lake Simcoe
- Beachfront rentals Lake Simcoe
- Townhouse rentals Lake Simcoe
- House rentals Lake Simcoe
- Waterfront rentals Lake Simcoe
- Lake house rentals Lake Simcoe
- Rentals with a sauna Lake Simcoe
- Private suite rentals Lake Simcoe
- Ski-in/ski-out rentals Lake Simcoe
- Cottage rentals Lake Simcoe
- Rentals with a patio Lake Simcoe
- Rentals with a kayak Lake Simcoe
- Cabin rentals Lake Simcoe
- Rentals with a hot tub Lake Simcoe
- Rentals with pools Lake Simcoe
- Bungalow rentals Lake Simcoe
- Fitness-friendly rentals Lake Simcoe
- Luxury rentals Lake Simcoe
- Guesthouse rentals Ontario
- Guesthouse rentals Canada
- Blue Mountain Village
- Toronto Zoo
- Rouge National Urban Park
- Horseshoe Resort
- Snow Valley Ski Resort
- Cedar Park Resort
- Osler Bluff Ski Club
- Craigleith Ski Club
- Gull Lake
- Devil's Glen Country Club
- Port Carling Golf & Country Club
- Hockley Valley Resort - Golf, Spa and Ski
- Angus Glen Golf Club
- Lakeridge Ski Resort
- The Club At Bond Head
- Lake Joseph Golf Club
- Wooden Sticks Golf Club
- Muskoka Lakes Golf and Country Club
- Mount St. Louis Moonstone
- Muskoka Bay Resort
- Georgian Bay Islands National Park
- Windermere Golf & Country Club
- Dagmar Ski Resort
- Barrie Country Club