Chalet holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for chalet rentals in Simcoe County
Family-friendly chalet rentals
Chalet in Blue Mountain
4.79 out of 5 average rating, 348 reviewsCozy, 4 Bedroom Chalet, 10 min walk to Village
24–31 Jan
Chalet in Hawkestone
4.77 out of 5 average rating, 216 reviewsCharming Cottage near Lake Simcoe
3–10 Nov
Chalet in The Blue Mountains
4.83 out of 5 average rating, 153 reviewsOctagon Chalet firepit, sauna, mins to the Village
20–27 Mar
Chalet in Blue Mountains
4.78 out of 5 average rating, 144 reviewsEscape to Northview Chalet Blue Mountain
21–28 Oct
Chalet in The Blue Mountains
4.88 out of 5 average rating, 67 reviewsStylish Log Chalet w/ Hot tub Minutes to Village
6–13 Oct
Chalet in The Blue Mountains
4.89 out of 5 average rating, 79 reviewsBeautiful Spanish Style Chalet with hot tub
24–31 Oct
Chalet in The Blue Mountains
4.78 out of 5 average rating, 196 reviewsExecutive Chalet
22–29 May
Chalet in The Blue Mountains
4.68 out of 5 average rating, 75 reviewsHotTub ☆ Sauna ☆ Basketball ☆ Southwestern Chalet
4–11 Sep
Luxury chalet rentals
Chalet in The Blue Mountains
4.93 out of 5 average rating, 113 reviewsThe Caribou Chalet (hot tub, sauna, 7-bedroom, sle
18–25 Mar
Chalet in Mulmur
5.0 out of 5 average rating, 29 reviewsInto the Woods Log Home
6–13 Nov
Chalet in Shanty Bay
4.92 out of 5 average rating, 13 reviews6 BR Horseshoe Mountain top Luxury chalet
24 Jun – 1 Jul
Chalet in The Blue Mountains
4.93 out of 5 average rating, 61 reviews⭐ 10 Rooms Sleeps 20 Hot tub Chalet Near Lake
24–31 Oct
Chalet in The Blue Mountains
4.98 out of 5 average rating, 49 reviewsWalk To Ski Hill- HOT TUB & SAUNA
15–22 Oct
Chalet in The Blue Mountains
4.84 out of 5 average rating, 82 reviewsCozy upgraded Chalet Hot Tubs Sauna Fireplace
30 Jul – 6 Aug
Chalet in The Blue Mountains
4.95 out of 5 average rating, 80 reviews⭐ 10 Beds Sleeps 20 Hot tub Chalet Near Resort
27 Jun – 4 Jul
Chalet in The Blue Mountains
4.73 out of 5 average rating, 177 reviewsLarge & Cozy Updated Chalet!! With Mountainviews!!
2–9 Oct
Lakefront chalet rentals
Chalet in Gravenhurst
4.91 out of 5 average rating, 43 reviewsMuskoka Mist
24–31 Dec
Chalet in Mulmur
5.0 out of 5 average rating, 30 reviewsCountry Oasis - Your private 5 acre resort
17–24 Nov
Chalet in Gravenhurst
4.95 out of 5 average rating, 21 reviewsLakeside Retreat: Fire Pit, Fireplace, 1.5hr frTO
8–15 Sep
Chalet in The Blue Mountains
4.7 out of 5 average rating, 57 reviewsBlue View 10 - Aqua Center
17–24 Dec
Chalet in Georgina
5.0 out of 5 average rating, 4 reviewsCozy 4BR Lakefront Gem | Hot Tub, Paddle Boards
17–24 Oct
Chalet in Gravenhurst
4.94 out of 5 average rating, 17 reviewsLuxury waterfront log home.
9–16 Jul
Chalet in Port Severn
4.61 out of 5 average rating, 71 reviewsGorgeous Muskoka 3+1 Lake Front Cottage
4–11 Feb
Destinations to explore
- Chalet rentals Canada
- Chalet rentals Ontario
- Loft rentals Simcoe County
- Apartment rentals Simcoe County
- House rentals Simcoe County
- Beachfront rentals Simcoe County
- Pet-friendly rentals Simcoe County
- Rentals with breakfast Simcoe County
- Bed and breakfasts Simcoe County
- Boutique hotel rentals Simcoe County
- Rentals with a patio Simcoe County
- Villa rentals Simcoe County
- Hotel rentals Simcoe County
- Rentals with a firepit Simcoe County
- Smoking-friendly rentals Simcoe County
- Waterfront rentals Simcoe County
- Private suite rentals Simcoe County
- Rentals with a fireplace Simcoe County
- Rentals with a washing machine and dryer Simcoe County
- Bungalow rentals Simcoe County
- Cottage rentals Simcoe County
- Guest house rentals Simcoe County
- Tiny house rentals Simcoe County
- Ski-in/ski-out rentals Simcoe County
- Monthly Rentals Simcoe County
- Rentals with pools Simcoe County
- Rentals with a hot tub Simcoe County
- Farm stay rentals Simcoe County
- Family-friendly rentals Simcoe County
- Townhouse rentals Simcoe County
- Rentals with an EV charger Simcoe County
- Rentals with a sauna Simcoe County
- Rentals with lake access Simcoe County
- Rentals with outdoor seating Simcoe County
- Fitness-friendly rentals Simcoe County
- Flat rentals Simcoe County
- Family-friendly rentals Simcoe County
- Rentals with a kayak Simcoe County
- Rentals with beach access Simcoe County
- Cabin rentals 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