House
10.0(28 Reviews)
1 Bedroom
2 Guests
Parking
Pool
Balcony/Terrace
Kitchen
US $205/Night
7 Nights - US $1,432
Simcoe Winter Rentals & Holiday Homes
Discover winter rentals Simcoe - We found 48 exact matches
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Compare Winter Rental in Simcoe
10.0
Apartment
5 Bedrooms
12 Guests
- Parking
View- Kitchen
Air Conditioner
US $197/Night
7 Nights - US $1,379
US $257/Night
7 Nights - US $1,801
House
9.8(18 Reviews)
2 Bedrooms
4 Guests
- Parking
Ocean View- Balcony/Terrace
- View
US $219/Night
7 Nights - US $1,530
Other
8.6(82 Reviews)
10 Bedrooms
29 Guests
- Parking
- View
Child Friendly
Sports/Activities
US $136/Night
7 Nights - US $950
Condo
9.8(15 Reviews)
1 Bedroom
3 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $208/Night
7 Nights - US $1,453
US $74/Night
7 Nights - US $517
Condo
9.8(11 Reviews)
2 Bedrooms
5 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $162/Night
7 Nights - US $1,137
US $99/Night
7 Nights - US $696
Condo
9.6(8 Reviews)
2 Bedrooms
5 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $235/Night
7 Nights - US $1,644
US $81/Night
7 Nights - US $569
Cabin
9.6(8 Reviews)
1 Bedroom
2 Guests
Pet Friendly
Toiletries
Bedding/Linens
Designated Smoking Area
US $134/Night
7 Nights - US $940
House
9.0(2 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $184/Night
7 Nights - US $1,291
House
9.0(2 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $162/Night
7 Nights - US $1,134
Cabin
1 Bedroom
5 Guests
- Ocean View
- View
- Kitchen
- Air Conditioner
US $277/Night
7 Nights - US $1,941
Cabin
1 Bedroom
3 Guests
- Ocean View
- View
- Kitchen
- Air Conditioner
US $210/Night
7 Nights - US $1,469
Cabin
1 Bedroom
3 Guests
- Ocean View
- View
- Kitchen
- Air Conditioner
US $210/Night
7 Nights - US $1,469
New
House
1 Bedroom
2 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $188/Night
7 Nights - US $1,319
House
10.0(15 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $271/Night
7 Nights - US $1,899
House
9.8(36 Reviews)
3 Bedrooms
6 Guests
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
US $291/Night
7 Nights - US $2,037
House
9.8(20 Reviews)
5 Bedrooms
10 Guests
- Hot Tub
- Parking
- Pool
Spa
US $682/Night
7 Nights - US $4,775
House
9.4(16 Reviews)
3 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $284/Night
7 Nights - US $1,990
New
House
9.0(2 Reviews)
5 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $389/Night
7 Nights - US $2,725
Bed & Breakfast
8.0(1 Review)
4 Bedrooms
9 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $318/Night
7 Nights - US $2,229
About Simcoe Winter Rental on Casai.com
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 48 accommodations for your upcoming winter getaway, whether you're dreaming of azure waters and sun-kissed beaches or charming coastal towns.
At Casai, we present a diverse array of listings for holiday homes and villas nestled in the picturesque landscapes of the Mediterranean and the Caribbean. From luxurious villas overlooking crystal-clear waters to charming holiday homes nestled amidst palm-fringed shores, our curated selection caters to every preference and ensures an unforgettable retreat.
Indulge in the epitome of luxury with our Mediterranean and Caribbean villas, boasting opulent amenities such as private pools, spacious outdoor terraces, serene gardens, and breathtaking ocean views. Whether you're seeking a romantic escape, a family adventure, or a group getaway, our listings offer the perfect blend of comfort and sophistication.
Escape the winter chill and bask in the warmth of the Mediterranean or Caribbean sun. Explore our collection of holiday homes and villas, meticulously curated to provide the ultimate sanctuary for your winter retreat. With Casai, your dream vacation awaits.
Winter Rental: Explore Top Destinations
Frequently Asked Questions About Simcoe Winter Rentals
What are the top rated Winter Rentals in Simcoe?
There are a lot of options in Simcoe. If you plan on staying in the Simcoe 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:
- Family stylish house min to Lake Erie/Port dover - fits 10
- Private Castle Retreat | 6 Luxury Suites, WEDDINGS, River & Waterfall & Gardens
- Charming Oasis Retreat
- - Hillside Shores Cottage – Scenic Decks, Cozy Vibes & Private Owned Beach
- Cottage with Pool, Dock and close to Sandy Beach
- Cozy waterfront cottage in a tranquil area
- River front cottage close to the beach
- Surf Vibes|California Cool design | Close to beach
- Beach-chic | Palm Springs design | Close to beach
- All Season Tiny Home in Forest with Sauna, Hot Tub & Wifi
How much does it cost to rent a place to stay near Simcoe in the wintertime?
The average cost for winter rentals in Simcoe is $301 per night. Casai has a wide list of great winter places to stay near Simcoe that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Simcoe that allow pets?
Yes, here are the top cottage/chalet rentals in Simcoe that allow you to bring your pet or dog:
- ForTwo guest house a place to relax, enjoy nature, beaches, trails, wineries.
- Fully furnished 5 BR,6 beds,4 WR Near Port Dover, Norfolk County Simcoe
- Clonmel Castle
- Bright, clean, central to downtown Dover. Short walk to shops, pier and beach.
See all pet-friendly vacation rentals in Simcoe on Casai.com
Do you have any winter rentals in Simcoe that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Simcoe to find what works for you.
Are there winter accommodations in Simcoe that have indoor swimming pools?
As of 2026, the data from Casai.com shows that there are over 48 private swimming pools or indoor pools accommodations near Simcoe along with other great amenities.
Do any winter holiday rentals in Simcoe have hot tubs?
About 48 holiday rentals in Simcoe boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Simcoe?
Yes, there are many luxury places to stay in Simcoe for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Simcoe with all the best amenities for your next trip.
