Simcoe County Winter Rental
Condo
10.0(86 Reviews)
1 Bedroom
1 Bath
4 Guests
630 ft²
Oceanfront
Parking
Pool
Ocean View
US $185/Night
7 Nights - US $1,292
House
10.0(17 Reviews)
1 Bedroom
1 Bath
4 Guests
10763.91 ft²
Private Pool- Oceanfront
Hot Tub- Parking
US $188/Night
7 Nights - US $1,319
US $184/Night
7 Nights - US $1,291
House
10.0(77 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $186/Night
7 Nights - US $1,302
Villa
10.0(8 Reviews)
3 Bedrooms
3 Baths
6 Guests
10763.91 ft²
- Oceanfront
Breakfast- Parking
Skiing
US $333/Night
7 Nights - US $2,329
Apartment
10.0(46 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $179/Night
7 Nights - US $1,252
House
10.0(6 Reviews)
2 Bedrooms
3 Baths
6 Guests
904.17 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $244/Night
7 Nights - US $1,711
Cottage
10.0(40 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $246/Night
7 Nights - US $1,721
House
10.0(5 Reviews)
4 Bedrooms
3 Baths
8 Guests
2454.17 ft²
- Parking
- Air Conditioner
Internet
Child Friendly
US $204/Night
7 Nights - US $1,429
House
10.0(33 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $391/Night
7 Nights - US $2,738
Ski Chalet
10.0(3 Reviews)
4 Bedrooms
3 Baths
8 Guests
2002.09 ft²
Private Beach- Oceanfront
- Hot Tub
- Breakfast
US $1,319/Night
7 Nights - US $9,233
Cabin
10.0(32 Reviews)
1 Bedroom
1 Bath
5 Guests
400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $166/Night
7 Nights - US $1,159
Why Choose Rent By Owner for your Simcoe County Winter Rental?
What makes our Winter Rental special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Simcoe County
How to Book Your Simcoe County Winter Rental
What's our booking process?
Our platform allows you to browse a curated selection of winter rental. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Simcoe County
Common Winter Rental Amenities
What amenities can you expect?
Our Winter Rental are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Simcoe County, ON
Central Ontario
Barrie - Orillia
Wasaga Beach
Collingwood
Innisfil
Oro-Medonte
Barrie
Ramara
Severn
Orillia
Simcoe County Winter Rental Frequently Asked Questions
1. What are the top Winter Rentals in Simcoe County?
There are a lot of options in Simcoe County. If you plan on staying in the Simcoe County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Winter Rentals in Simcoe County:
- HOT TUB-Natural paradise, timber frame, sauna, close to Casino and ski hill.
- Waterfront home, city/sunset views & steps to beach, Sleeps 12 + new hot tub
- Beautiful & Private Mid Century Modern Country-House on 10 Acres near Caledon
- Waterfront & Pvt Beach 120’Shoreline: SHALLOW/Sandy: Perfect for Little Kids!
- Amazing fully upgraded 3 bedroom+ new furniture, 1 full bath lake property
- Modern 5-bedroom house close to Ski and Forest Trails
- Stunning Waterfront Luxurious Lakehouse 45 mins from Toronto! Great for families
- Spectacular Waterfront three Bedroom Home!
- STUNNING LAKEFRONT VIEWS. Beautiful, ground floor unit. Lighthouse Point.
- Luxury Beach House With Incredible Sunset Views
2. How many Winter Rentals are available in Simcoe County?
Currently, the total number of properties listed by RBO in 2026 is over 2001 in the Simcoe County area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Simcoe County.
More Rentals You May Like Near Simcoe County
House
10.0(2 Reviews)
4 Bedrooms
4 Baths
8 Guests
3003.13 ft²
- Oceanfront
- Breakfast
EV Charge Station- Parking
US $484/Night
7 Nights - US $3,391
Condo
10.0(25 Reviews)
1 Bedroom
1 Bath
2 Guests
700 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $191/Night
7 Nights - US $1,334
Condo
10.0(21 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $277/Night
7 Nights - US $1,942
Ski Chalet
10.0(20 Reviews)
2 Bedrooms
1 Bath
5 Guests
1000 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $257/Night
7 Nights - US $1,799
House
10.0(17 Reviews)
1 Bedroom
1 Bath
3 Guests
500 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $159/Night
7 Nights - US $1,114
Condo
10.0(12 Reviews)
1 Bedroom
2 Baths
2 Guests
- Oceanfront
- Parking
- Pool
Spa
US $340/Night
7 Nights - US $2,381
House
10.0(12 Reviews)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
- Oceanfront
- Breakfast
- Parking
- Ocean View
US $216/Night
7 Nights - US $1,512
House
10.0(11 Reviews)
2 Bedrooms
2 Baths
6 Guests
915 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $370/Night
7 Nights - US $2,593
Condo
10.0(11 Reviews)
2 Bedrooms
2 Baths
5 Guests
850 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $245/Night
7 Nights - US $1,718
Condo
10.0(11 Reviews)
1 Bedroom
1 Bath
5 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
US $149/Night
7 Nights - US $1,042
Cottage
10.0(11 Reviews)
2 Bedrooms
1 Bath
5 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $134/Night
7 Nights - US $936
Cottage
10.0(10 Reviews)
1 Bedroom
1 Bath
4 Guests
500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Child Friendly
US $163/Night
7 Nights - US $1,140
