
Holiday rentals in Simcoe County
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Simcoe County
Guests agree: these stays are highly rated for location, cleanliness and more.

Fire & Ice Spa w/ Private Sauna!
Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh and unwind in your very own private spa experience which includes large infrared sauna, 3 indoor fireplaces and outdoor fire table. Kiss those winter blues away while you warm up in the most cozy suite, perfect for a romantic getaway. Every stay includes a bottle of bubbly to toast with the one who is most important to you! Make Fire & Ice your next vacation destination and reconnect in a most romantic, relaxing suite!

The Loft at Bryn Mawr House
Welcome to your ideal Ontario getaway! Our full luxury suite offers a king-size bed, living room with a pull-out , fully-equipped kitchen, and ample parking . Enjoy our 11 acres, a fire pit, pond, and horseshoe area. Explore numerous provincial snowmobile trails, hiking, kayaking and canoeing in the Minesing Wetlands We're central to Blue Mountain, Horseshoe Valley and Snow Valley ski resorts. And Wasaga Beach is just around the corner! Your unforgettable Ontario adventure awaits – book now!

Off-grid Glamping Dome Nestled in the Woods
Welcome to our private campsite in Utopia, ON. Our family’s glamping dome is your chance to experience a unique getaway surrounded by the sights & sounds of nature. Amenities include camping essentials & some glamping perks: king size bed, bbq, fireplace, Indoor incineration toilet, soap & water, outdoor shower (summer only), kettle, cooking utensils. Nearby is Purple Hill Lavender Farms, Drysdale's Tree Farm, Tiffin Conservation Area, Nottawasaga & golf courses. Wasaga Beach is 30 min away.

Bird Haven Log Cabin
Embrace the log cabin charm. Bright & cheery, historic & unique. Fully renovated with all the modern conveniences. Starlink internet and EV charger. Close to an extensive variety of activities, walking trails, Lake Simcoe, lake side parks, restaurants, golf courses, skydiving, antique markets, shopping, casino & racetrack. Living room features comfy sectional, cathedral ceilings, floor-ceiling stone fireplace & 50" TV. Well equipped brand new kitchen. Dine inside or al fresco on the patio.

Saltbox by the Bay | Views, Bikes, Beaches & Vetta
*SUMMER AVAILS* *GUEST BIKES* Welcome to Saltbox by the Bay, a cozy vintage cottage with beautiful views & luxe amenities. Perfect as a couples getaway, small family/friends vacation or solo retreat. Ease into slow living, cook your favourite meals, play boardgames & albums, as you watch birds & sunsets over the bay. Walk or borrow our bikes for the Tay Shore Trail, visit nearby beaches & Quayle's Brewery, pamper yourself at Vetta Nordic Spa & explore charming towns around Georgian Bay.

Blue Mountain Gallery Getaway
Welcome to a cozy family escape featuring a stunning gallery wall showcasing scenic photography of South Georgian Bay. This peaceful retreat is just minutes from Blue Mountain Village or downtown Collingwood. Listen to the soothing sounds of the Cranberry Marsh Wetland, or walk to nearby Georgian Bay. Whether you’re hitting the slopes, the spas or the shops, unwind in a space that’s as inspiring as it is relaxing. Send us a message if you have any questions — we're always happy to help!

Hytte Away - Cabin Retreat with Sauna
We welcome you to Hytte Away, a thoughtfully designed private cabin retreat for two nestled on 54 acres of forest land. Offering you the opportunity to disconnect and reconnect. The property features an amazing sauna and cold plunge experience, hiking trails (currently being worked on from ice storm) and the perfect little cabin to do some actual relaxing. The space is unique and the best approach is to think of it as a glamping experience. Follow us on insta for more - hytteaway

The Hideout | Garden Suite • Coffee Station • BBQ
Welcome to The Hideout – Your Cozy Garden Escape 🌿✨ The Hideout is a stylish one-bedroom, one-bathroom garden suite designed for comfort and relaxation. Thoughtfully decorated in calming blue and warm brown tones, with elegant gold accents, this inviting retreat blends modern sophistication with a warm, homey atmosphere. Whether you’re here for a weekend getaway or a short stay, The Hideout is perfectly situated just minutes from Barrie’s downtown, waterfront, and local attractions.

Bunkie On The River
Welcome to our four season bunkie retreat on the river. Leave the world behind and seek comfort and peace at Riverside Ranch. Imagine starting your day reconnecting with nature amidst wooded walking trails. Along your walk you see geese swimming in the river, goats exploring the woods, and Highland cattle grazing in the pasture. Upon return, you open the door to the crackle & pop of a toasty wood burning sauna, followed by an icy cold plunge in the river. *No air-conditioning*

Deerleap Glamping Dome
Located close to the city, our four-season glamping dome offers a peaceful and unique escape. In winter, the snow-covered landscape creates a magical scene, while inside, the wood pellet stove keeps the dome exceptionally warm and cozy. Nestled on 10 acres of picturesque land and a stunning pond view, Enjoy everything you need—from upscale sanitary facilities to fast Wi-Fi. Whether you’re celebrating a birthday, an anniversary, or simply seeking quiet time in nature.

The Bubble Glamping Dome
Escape to a luxury geodesic dome on our scenic farm, nestled at the edge of the forest. Fully equipped with heating, cooling, a private washroom, deck, and hot tub, it’s the perfect blend of comfort and nature. Explore the farm, meet our sheep, chickens, and livestock guardian dog, or hike over 100 acres of connected regional forest. Whether you’re relaxing under the stars or adventuring outdoors, this unique glamping retreat promises an unforgettable experience.

Little Lake Escape | Waterfront 2 Bedroom Getaway
Cozy 2-bedroom lakefront retreat on Little Lake, just minutes from downtown Midland. Enjoy the perfect mix of convenience and seclusion, with peaceful surroundings and beautiful water views. This charming getaway features a warm, inviting interior, a gas-burning fireplace, and a bright sunroom to relax year-round. Ideal for couples or small families looking to unwind by the water while staying close to local shops, restaurants, and attractions.
Popular amenities for Simcoe County holiday rentals
Other great holiday rentals in Simcoe County

Bright MCM 2 Bedroom Walk Up with Private Deck/BBQ

Welcoming Waterfront Cottage

Farmhouse next to Bike, Hike, Ski Forest Trails

Tranquil Forest Oasis

Charming Pioneer Cabin in the Woods

The Secret Garden - Dome Escape

The Cozy Coop - Tiny Cottage

Casa Doma | Unique 3BR Muskoka Retreat + Hot Tub
Destinations to explore
- Cabin rentals Simcoe County
- Boutique hotels Simcoe County
- Rentals with an EV charger Simcoe County
- Ski-in/ski-out rentals Simcoe County
- Private suite rentals Simcoe County
- Holiday home rentals Simcoe County
- Rentals with a washing machine and dryer Simcoe County
- Loft rentals Simcoe County
- Hotel rooms Simcoe County
- Rentals with pools Simcoe County
- House rentals Simcoe County
- Smoking-friendly rentals Simcoe County
- Bungalow rentals Simcoe County
- Farm stay rentals Simcoe County
- Rentals with a cinema Simcoe County
- Rentals with breakfast Simcoe County
- Cottage rentals Simcoe County
- Townhouse rentals Simcoe County
- Rentals with a fireplace Simcoe County
- Guest house rentals Simcoe County
- Bed and breakfasts Simcoe County
- Flat rentals Simcoe County
- Beachfront rentals Simcoe County
- Chalet rentals Simcoe County
- Waterfront rentals Simcoe County
- Rentals with beach access Simcoe County
- Fitness-friendly rentals Simcoe County
- Rentals with outdoor seating Simcoe County
- Motorhome rentals Simcoe County
- Pet-friendly rentals Simcoe County
- Rentals with a hot tub Simcoe County
- Rentals with a patio Simcoe County
- Villa rentals Simcoe County
- Family-friendly rentals Simcoe County
- Luxury rentals Simcoe County
- Tiny house rentals Simcoe County
- Rentals with a firepit Simcoe County
- Apartment rentals Simcoe County
- Rentals with lake access Simcoe County
- Rentals with a sauna Simcoe County
- Rentals with a kayak Simcoe County
- Dome rentals Simcoe County
- Blue Mountain Village
- Snow Valley Ski Resort
- Mount St. Louis Moonstone
- Beaver Valley Ski Club
- Lakeridge Ski Resort
- Osler Bluff Ski Club
- Torrance Barrens Dark Sky Conservation Area
- Wasaga Beach Area
- Devil's Glen Country Club
- Dagmar Ski Resort
- Awenda Provincial Park
- Vaughan Mills
- Scandinave Spa Blue Mountain
- Burl's Creek Event Grounds
- Georgian Bay Islands National Park
- Kee To Bala
- Casino Rama Resort
- Wye Marsh Wildlife Centre
- Taboo Muskoka Resort & Golf
- Mono Cliffs Provincial Park
- Centennial Beach
- Bass Lake Provincial Park
- Forks of the Credit Provincial Park
- Balsam Lake Provincial Park





