House
10.0(72 Reviews)
2 Bedrooms
6 Guests
Private Pool
Parking
Pool
Balcony/Terrace
CA $691/Night
7 Nights - CA $4,839
Hampton Roads, VA Winter Rentals & Holiday Homes
Discover winter rentals Hampton Roads - We found 16675 exact matches
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Compare Winter Rental in Hampton Roads
10.0
Bed & Breakfast
10.0(11 Reviews)
1 Bedroom
4 Guests
EV Charge Station- Parking
View
Air Conditioner
CA $265/Night
7 Nights - CA $1,852
House
4 Bedrooms
8 Guests
Oceanfront
Hot Tub- Parking
Ocean View
CA $961/Night
7 Nights - CA $6,727
House
10.0(58 Reviews)
4 Bedrooms
10 Guests
- Private Pool
- Hot Tub
- Pool
- Ocean View
CA $678/Night
7 Nights - CA $4,745
Bed & Breakfast
10.0(8 Reviews)
1 Bedroom
6 Guests
- EV Charge Station
- Parking
- View
- Air Conditioner
CA $389/Night
7 Nights - CA $2,720
New
House
10.0(27 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $447/Night
7 Nights - CA $3,127
CA $536/Night
7 Nights - CA $3,749
House
10.0(8 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $369/Night
7 Nights - CA $2,585
House
10.0(7 Reviews)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
Internet
Child Friendly
CA $518/Night
7 Nights - CA $3,627
Condo
10.0(5 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $643/Night
7 Nights - CA $4,502
CA $843/Night
7 Nights - CA $5,898
New
House
10.0(2 Reviews)
4 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- View
Kitchen
CA $559/Night
7 Nights - CA $3,913
House
10.0(5 Reviews)
3 Bedrooms
7 Guests
- Parking
- View
- Kitchen
- Air Conditioner
CA $572/Night
7 Nights - CA $4,003
Condo
10.0(2 Reviews)
3 Bedrooms
10 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $176/Night
7 Nights - CA $1,230
New
Condo
10.0(2 Reviews)
2 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $113/Night
7 Nights - CA $792
Condo
10.0(1 Review)
4 Bedrooms
16 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $297/Night
7 Nights - CA $2,077
New
Condo
10.0(1 Review)
4 Bedrooms
16 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $283/Night
7 Nights - CA $1,982
House
10.0(1 Review)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
CA $204/Night
7 Nights - CA $1,426
New
Condo
10.0(1 Review)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $83/Night
7 Nights - CA $583
New
House
9.6(11 Reviews)
3 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $1,413/Night
7 Nights - CA $9,894
New
Condo
9.4(13 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $122/Night
7 Nights - CA $851
New
House
9.2(39 Reviews)
6 Bedrooms
16 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
CA $1,614/Night
7 Nights - CA $11,295
New
Condo
9.2(31 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $122/Night
7 Nights - CA $851
Condo
8.8(16 Reviews)
3 Bedrooms
10 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $166/Night
7 Nights - CA $1,165
About Hampton Roads Winter Rental on Casai.ca
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 16675 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 Hampton Roads Winter Rentals
What are the top rated Winter Rentals in Hampton Roads?
There are a lot of options in Hampton Roads. If you plan on staying in the Hampton Roads area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Hampton Roads:
- Cozy, Dog-friendly Duplex At The North End Short Walk To The Beach!
- Fantastic home in the heart of the VB Resort Area Walk to Beach, Boardwalk.
- Historic Cottage on Ware River Estate
- Breezy, Quaint, and Dog- Friendly North End duplex.
- Riverfront House, Dock, Hot Tub, Salt Pool, near beach, Free WiFi
- CLASSIC 1935 OCEANFRONT BEACH COTTAGE
- Don't miss out on fall dates and amazing rates. Great Location & Fido-friendly.
- Award Winning Ocean Front Architectural Gem [Home Share per VA Beach Zoning]
- Nags Head 2 blocks to beach, 3bdrms. Booking for late summer & fall. 5⭐reviews
- Ivey Coast 6BR, Sleeps 14,Pool,Hot Tub, pool table, arcade, 2 min walk to Ocean
How much does it cost to rent a place to stay near Hampton Roads in the wintertime?
The average cost for winter rentals in Hampton Roads is $549 per night. Casai has a wide list of great winter places to stay near Hampton Roads that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Hampton Roads that allow pets?
Yes, here are the top cottage/chalet rentals in Hampton Roads that allow you to bring your pet or dog:
- Ware Haven Cottage On The Ware River With Pool, Pier, And Kayaks.
- Avamere 206 Inn at Old Beach
- JL #367-b - Double Dog Dare - Oceanfront - Hot Tub - Pets
- Oceanside,Pool,Spa,PinBall,7MinWalk2Beach&Sound New
See all pet-friendly vacation rentals in Hampton Roads on Casai.ca
Do you have any winter rentals in Hampton Roads that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Hampton Roads to find what works for you.
Are there winter accommodations in Hampton Roads that have indoor swimming pools?
As of 2026, the data from Casai.ca shows that there are over 16675 private swimming pools or indoor pools accommodations near Hampton Roads along with other great amenities.
Do any winter holiday rentals in Hampton Roads have hot tubs?
About 16675 holiday rentals in Hampton Roads boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Hampton Roads?
Yes, there are many luxury places to stay in Hampton Roads for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Hampton Roads with all the best amenities for your next trip.
