House
10.0(18 Reviews)
2 Bedrooms
4 Guests
Kitchen
Air Conditioner
Internet
Child Friendly
CA $572/Night
7 Nights - CA $4,005
Cunningham Winter Rentals & Holiday Homes
Discover winter rentals Cunningham - We found 55 exact matches
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Compare Winter Rental in Cunningham
10.0
CA $1,222/Night
7 Nights - CA $8,556
House
9.6(65 Reviews)
1 Bedroom
2 Guests
Private Pool
Hot Tub
Parking
Pool
CA $443/Night
7 Nights - CA $3,102
Cottage
9.6(34 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
Ocean View
Balcony/Terrace
CA $427/Night
7 Nights - CA $2,988
Cottage
8.8(14 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $417/Night
7 Nights - CA $2,920
Cottage
10.0(63 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $381/Night
7 Nights - CA $2,663
House
10.0(58 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $384/Night
7 Nights - CA $2,687
Cottage
10.0(48 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $283/Night
7 Nights - CA $1,982
House
10.0(9 Reviews)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
Pet Friendly
CA $350/Night
7 Nights - CA $2,447
Cabin
10.0(6 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $580/Night
7 Nights - CA $4,059
House
9.8(15 Reviews)
1 Bedroom
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $334/Night
7 Nights - CA $2,341
Cabin
8.4(5 Reviews)
1 Bedroom
3 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $512/Night
7 Nights - CA $3,583
Cabin
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
CA $422/Night
7 Nights - CA $2,951
Cottage
1 Bedroom
2 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
CA $281/Night
7 Nights - CA $1,969
Bed & Breakfast
1 Bedroom
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $247/Night
7 Nights - CA $1,729
New
Other
1 Bedroom
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $344/Night
7 Nights - CA $2,409
House
10.0(7 Reviews)
4 Bedrooms
10 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
CA $2,116/Night
7 Nights - CA $14,810
House
9.6(11 Reviews)
7 Bedrooms
19 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $1,032/Night
7 Nights - CA $7,221
House
9.4(24 Reviews)
4 Bedrooms
13 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $1,038/Night
7 Nights - CA $7,265
House
9.4(11 Reviews)
3 Bedrooms
9 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $800/Night
7 Nights - CA $5,603
New
Other
3 Bedrooms
10 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $733/Night
7 Nights - CA $5,130
House
10.0(407 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $699/Night
7 Nights - CA $4,893
House
10.0(52 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $666/Night
7 Nights - CA $4,661
About Cunningham Winter Rental on Casai.ca
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 55 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 Cunningham Winter Rentals
What are the top rated Winter Rentals in Cunningham?
There are a lot of options in Cunningham. If you plan on staying in the Cunningham area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Cunningham:
- 10 Vineyards Within 10 Mi, EV charger & Mini Goats
- Fairwood Cottages- Both Cottages, Getaway Close to Town
- Mountain View Cabin in VA Wine Country
- Private cabin in wine country
- 1802 cottage once part of Monticello and owned by Thomas Jefferson
- Beautiful New Townhome with Mountain Views. Close to downtown!
- Ranchito: Near Keswick Hall & Local Vineyards
- Remodeled Cabin Rental Built in 1790 near Scottsville, Virginia
- Two Bedroom One Bath Cottage On 250 Acre Cattle Farm.
- Quarry House on Quiet Entry Farm | Near Wineries
How much does it cost to rent a place to stay near Cunningham in the wintertime?
The average cost for winter rentals in Cunningham is $497 per night. Casai has a wide list of great winter places to stay near Cunningham that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Cunningham that allow pets?
Yes, here are the top cottage/chalet rentals in Cunningham that allow you to bring your pet or dog:
- Entire Cottage on Equestrian Farm with Zebras
- Ranchito
- Albemarle Estate at Trump Winery
- Cottage on quiet farm close to town and wineries
See all pet-friendly vacation rentals in Cunningham on Casai.ca
Do you have any winter rentals in Cunningham that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Cunningham to find what works for you.
Are there winter accommodations in Cunningham that have indoor swimming pools?
As of 2026, the data from Casai.ca shows that there are over 55 private swimming pools or indoor pools accommodations near Cunningham along with other great amenities.
Do any winter holiday rentals in Cunningham have hot tubs?
About 55 holiday rentals in Cunningham boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Cunningham?
Yes, there are many luxury places to stay in Cunningham for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Cunningham with all the best amenities for your next trip.
