Ontario Winter Rentals & Holiday Homes

Discover winter rentals Ontario - We found 20067 exact matches

Clyde Hall Bed and Breakfast
FromUS $383 per night
|
10.0 (29 Reviews)
4 Bedrooms 16 Guests
Slopeside Condo - Wifi, Linens/Towels, Ski In/Out
9.6 (37 Reviews)
1 Bedroom 4 Guests
Chalet Styled Townhome, Very Clean, Great Condition.
10.0 (296 Reviews)
2 Bedrooms 6 Guests
Stylish Downtown Kingsville Getaway with Putting Green, Firepit & Games
|
10.0 (12 Reviews)
3 Bedrooms 8 Guests
Nature Oasis Mar Suite
FromUS $181 per night
10.0 (11 Reviews)
1 Bedroom 3 Guests
Downtown Toronto Tree-Top Gem
10.0 (169 Reviews)
2 Bedrooms 3 Guests
Vintage Farmhouse with Hot Tub on Vineyard
|
10.0 (9 Reviews)
3 Bedrooms 8 Guests
Awaken to nature’s beauty at Whispering Pines Retreat!
10.0 (143 Reviews)
1 Bedroom 4 Guests
The VICTORIA: Petit Appartment
FromUS $180 per night
10.0 (110 Reviews)
1 Bedroom 3 Guests
Relaxing retreat in the country
10.0 (104 Reviews)
2 Bedrooms 5 Guests
-Quiet Mountainview Retreat with Private Pool
10.0 (94 Reviews)
2 Bedrooms 4 Guests
Loon's Nest on Superior - An adventure for every season!
10.0 (93 Reviews)
2 Bedrooms 5 Guests
Waterfront Vacation Rental 5 Min. From Sandbanks Beach
10.0 (91 Reviews)
2 Bedrooms 6 Guests

About Ontario Winter Rental on Vacation Cottage

At Vacation Cottage, we showcase a diverse array of accommodations in Ontario, ON perfect for your winter retreat or seasonal escape. Our listings encompass hotels, private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments, ensuring travelers find their ideal accommodation. Vacation Cottage's winter vacation homes boast premier amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Whether you're seeking to escape the snow or embrace it, Vacation Cottage facilitates your connection to the finest cabins, bungalows, lodges, cottages, and the best accommodations in both sunny retreats and ski resorts. Vacation Cottage ensures your winter getaway becomes an unforgettable experience.

Vacation Cottage presents luxury options for travelers seeking to rent a place in Ontario. To access these benefits and book your winter vacation home, simply utilize the Vacation Cottage filter option. Enter your travel dates, refine your search with filters for property type and amenities, then choose from our extensive list of exceptional winter vacation rentals hassle-free. Our interactive map further enhances your experience, allowing you to explore destinations worldwide or within Ontario and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.

Frequently Asked Questions About Ontario Winter Rentals

What are the top rated Winter Rentals in Ontario?

There are a lot of options in Ontario. If you plan on staying in the Ontario area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Ontario:

How much does it cost to rent a place to stay near Ontario in the wintertime?

The average cost for winter rentals in Ontario is $392 per night. Vacation Cottage has a wide list of great winter places to stay near Ontario that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

Are there any winter cottages/chalets in Ontario that allow pets?

Yes, here are the top cottage/chalet rentals in Ontario that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Ontario on Vacation Cottage

Do you have any winter rentals in Ontario that are suitable for families?

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Ontario to find what works for you.

Are there winter accommodations in Ontario that have indoor swimming pools?

As of 2026, the data from Vacation Cottage shows that there are over 20067 private swimming pools or indoor pools accommodations near Ontario along with other great amenities.

Do any winter holiday rentals in Ontario have hot tubs?

About 20067 holiday rentals in Ontario boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Are there luxury winter rentals in Ontario?

Yes, there are many luxury places to stay in Ontario for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Ontario with all the best amenities for your next trip.