Condo
10.0(359 Reviews)
2 Bedrooms
6 Guests
Oceanfront
Parking
Ocean View
Balcony/Terrace
£187/Night
7 Nights - £1,309
Hampton Roads Winter Rentals & Holiday Homes
Discover winter rentals Hampton Roads - We found 16385 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
£142/Night
7 Nights - £991
Bed & Breakfast
10.0(75 Reviews)
1 Bedroom
Breakfast- Parking
- Balcony/Terrace
Kitchen
£184/Night
7 Nights - £1,289
Condo
10.0(281 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
£200/Night
7 Nights - £1,398
Bed & Breakfast
10.0(8 Reviews)
1 Bedroom
6 Guests
- EV Charge Station
- Parking
- View
- Air Conditioner
£240/Night
7 Nights - £1,679
Condo
10.0(189 Reviews)
2 Bedrooms
6 Guests
Private Pool- Oceanfront
- Parking
Pool
£326/Night
7 Nights - £2,283
House
10.0(7 Reviews)
4 Bedrooms
10 Guests
Hot Tub- Parking
Spa
Internet
£496/Night
7 Nights - £3,473
Condo
10.0(186 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
£124/Night
7 Nights - £870
£286/Night
7 Nights - £2,006
House
10.0(182 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
£151/Night
7 Nights - £1,055
£451/Night
7 Nights - £3,155
Condo
10.0(181 Reviews)
1 Bedroom
4 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
£121/Night
7 Nights - £850
House
10.0(5 Reviews)
3 Bedrooms
7 Guests
- Parking
- View
- Air Conditioner
- Internet
£306/Night
7 Nights - £2,142
Condo
10.0(161 Reviews)
1 Bedroom
3 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
£268/Night
7 Nights - £1,874
House
10.0(136 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
£161/Night
7 Nights - £1,125
Condo
10.0(122 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
£336/Night
7 Nights - £2,354
Cottage
10.0(121 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
£197/Night
7 Nights - £1,380
Cottage
10.0(116 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
£271/Night
7 Nights - £1,897
House
10.0(96 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£370/Night
7 Nights - £2,593
Condo
10.0(96 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
£319/Night
7 Nights - £2,234
Condo
10.0(92 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
£341/Night
7 Nights - £2,385
House
10.0(92 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
£250/Night
7 Nights - £1,752
Condo
10.0(86 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
£302/Night
7 Nights - £2,116
Apartment
10.0(85 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
£206/Night
7 Nights - £1,440
About Hampton Roads Winter Rental on BedroomVillas.co.uk
At BedroomVillas, we feature a wide range of listings for accommodations in Hampton Roads, VA that are perfect for your winter trip or seasonal escape. Our listings include hotels, private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that travelers are sure to love. BedroomVillas winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Whether you are escaping the snow or running to it, BedroomVillas helps connect you to the best cabins, bungalows, lodges, and villas, as well as the best places to stay in both sun and ski resorts. BedroomVillas will make your winter getaway an unforgettable experience.
BedroomVillas offers luxury finds for travelers planning on renting a place in Hampton Roads, to enjoy these benefits and to book your winter vacation homes, go to the BedroomVillas filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of incredible winter vacation rentals without hassle. Our interactive map is also available, so you can view destinations spanning the globe or around Hampton Roads and unlock even more amazing deals. Relax with BedroomVillas.
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:
- Cottage on a Private Island in the York River
- Historic Cottage on Ware River Estate
- Riverfront House, Dock, Hot Tub, Salt Pool, near beach, Free WiFi
- Nags Head OCEANSIDE! 3 Bedroom 4 Bath Home! 5 Star Property! 2 Night Minimum!
- 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
- Relax, Rejuvenate, and Refresh
- 321 Packed with Amenities and Close to the Beach!
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 $541 per night. BedroomVillas.co.uk 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:
- Cozy, Dog-friendly Duplex At The North End Short Walk To The Beach!
- Avamere 206 Inn at Old Beach
- Hornsby House Inn
- Breezy, Quaint, and Dog- Friendly North End duplex.
See all pet-friendly vacation rentals in Hampton Roads on BedroomVillas.co.uk
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 BedroomVillas.co.uk shows that there are over 16385 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 16385 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.
