Chalet vacation rentals in Simcoe County
Find and book unique chalets on Airbnb
Top-rated chalet rentals in Simcoe County
Guests agree: these chalets 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 Simcoe County chalet rentals
Family-friendly chalet rentals
Chalet in The Blue Mountains
4.64 out of 5 average rating, 28 reviewsVillage Close, Hot Tub, BBQ Patio, Large Groups
Chalet in The Blue Mountains
4.9 out of 5 average rating, 77 reviewsStylish Log Chalet w/ Hot tub Minutes to Village
Chalet in Creemore
5 out of 5 average rating, 26 reviewsBreathtaking Creemore Country Escape #Spa #Gym
Chalet in The Blue Mountains
4.83 out of 5 average rating, 162 reviewsOctagon Chalet firepit, sauna, close to theVillage
Chalet in The Blue Mountains
4.6 out of 5 average rating, 258 reviewsBeach Pass w/ Mountain Golf View in Village
Chalet in The Blue Mountains
4.88 out of 5 average rating, 94 reviewsRustic Spanish Chalet inthe Heart of Nature/hottub
Chalet in Blue Mountain
4.79 out of 5 average rating, 359 reviewsCozy, 4 Bedroom Chalet, 10 min walk to Village
Chalet in The Blue Mountains
4.8 out of 5 average rating, 59 reviewsChalet Getaway 4 Seasonal Escape
Luxury chalet rentals
Chalet in The Blue Mountains
4.87 out of 5 average rating, 23 reviewsAll-Season 8BR Vacation Chalet at Blue Mountains
Chalet in Collingwood
4.94 out of 5 average rating, 81 reviewsThe woodlands Sleeps 20! HOT TUB Volleyball Court
Chalet in Collingwood
4.93 out of 5 average rating, 14 reviews*NEW* Naturskön Cottage | Mountain Views | Hot Tub
Chalet in The Blue Mountains
4.86 out of 5 average rating, 69 reviews8 bedrooms+Pool+Sauna (leftbank Onsis chalet)
Chalet in The Blue Mountains
4.62 out of 5 average rating, 21 reviewsBlue Mountain Gem (R) near the Village
Chalet in The Blue Mountains
5 out of 5 average rating, 6 reviewsIndoor Pool & Hot Tub, Steps to Ski Lift
Chalet in The Blue Mountains
4.71 out of 5 average rating, 105 reviewsBlue Birds Inn Collingwood, The Blue Mountains
Chalet in The Blue Mountains
4.91 out of 5 average rating, 224 reviewsRelax at The Mountaintop Chalet (sleeps 16)
Lakefront chalet rentals
Chalet in Gravenhurst
4.74 out of 5 average rating, 38 reviewsLakefront Retreat, Cathedral Ceilings & Fireplace
Chalet in Gravenhurst
4.95 out of 5 average rating, 21 reviewsBeautiful waterfront log home
Chalet in The Blue Mountains
4.68 out of 5 average rating, 68 reviewsBlue View 10 - Aqua Center
Chalet in Georgina
4.94 out of 5 average rating, 18 reviews4BR Luxe Lakefront Gem | Hot Tub, Paddle Boards
Chalet in Gravenhurst
4.9 out of 5 average rating, 59 reviewsMuskoka Mist
Chalet in Severn Bridge
5 out of 5 average rating, 14 reviewsThe Cozy Camp Cottage and Jean Lodge
Chalet in Port Severn
4.62 out of 5 average rating, 76 reviewsPrivate Scenic Muskoka Lakefront Cottage (Hot Tub)
Chalet in Mulmur
5 out of 5 average rating, 35 reviewsCountry Oasis - 5 private acres with hot tub
Destinations to explore
- Chalet rentals Canada
- Chalet rentals Ontario
- Condo rentals Simcoe County
- Rentals with lake access Simcoe County
- Monthly Rentals Simcoe County
- Fitness-friendly rentals Simcoe County
- Rentals with a washer and dryer Simcoe County
- Rentals with breakfast Simcoe County
- Pet-friendly rentals Simcoe County
- Bed and breakfasts Simcoe County
- Family-friendly rentals Simcoe County
- Rentals with a fireplace Simcoe County
- Boutique hotel rentals Simcoe County
- Townhouse rentals Simcoe County
- Smoking-friendly rentals Simcoe County
- Apartment rentals Simcoe County
- Kid-friendly rentals Simcoe County
- Hotel rentals Simcoe County
- Rentals with pools Simcoe County
- Rentals with a patio Simcoe County
- Rentals with outdoor seating Simcoe County
- Tiny house rentals Simcoe County
- Beachfront rentals Simcoe County
- Ski-in/ski-out rentals Simcoe County
- Guesthouse rentals Simcoe County
- Cabin rentals Simcoe County
- Loft rentals Simcoe County
- Bungalow rentals Simcoe County
- Rentals with a kayak Simcoe County
- House rentals Simcoe County
- Cottage rentals Simcoe County
- Rentals with a hot tub Simcoe County
- Rentals with a fire pit Simcoe County
- Rentals with a sauna Simcoe County
- Private suite rentals Simcoe County
- Farmstay rentals Simcoe County
- Villa rentals Simcoe County
- Waterfront rentals Simcoe County
- Rentals with an EV charger Simcoe County
- Rentals with beach access Simcoe County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Things to do Canada
- Entertainment Canada
- Food and drink Canada
- Sightseeing Canada
- Wellness Canada
- Art and culture Canada
- Sports activities Canada
- Nature and outdoors Canada
- Things to do Ontario
- Nature and outdoors Ontario
- Entertainment Ontario
- Sports activities Ontario
- Food and drink Ontario
- Sightseeing Ontario
- Art and culture Ontario
- Things to do Simcoe County
- Nature and outdoors Simcoe County
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes