Hampton Roads Winter Rental
Cottage
10.0(282 Reviews)
1 Bedroom
1 Bath
4 Guests
Fireplace/Heating
Ocean View
Balcony/Terrace
View
£142/Night
7 Nights - £991
Bed & Breakfast
10.0(10 Reviews)
1 Bedroom
1 Bath
4 Guests
398.26 ft²
- Fireplace/Heating
- View
Parking
Air Conditioner
£174/Night
7 Nights - £1,215
Bed & Breakfast
10.0(215 Reviews)
1 Bedroom
1 Bath
Spa
Pool- Balcony/Terrace
Breakfast
£198/Night
7 Nights - £1,389
Cottage
10.0(188 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
Kitchen
£255/Night
7 Nights - £1,787
Bed & Breakfast
10.0(8 Reviews)
1 Bedroom
2 Baths
6 Guests
850.35 ft²
- Fireplace/Heating
- View
- Parking
- Air Conditioner
£238/Night
7 Nights - £1,665
House
10.0(114 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
£111/Night
7 Nights - £775
House
10.0(7 Reviews)
4 Bedrooms
4 Baths
8 Guests
1797.57 ft²
Oceanfront- Fireplace/Heating
- Pool
- Ocean View
£433/Night
7 Nights - £3,030
House
10.0(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
£306/Night
7 Nights - £2,146
House
10.0(5 Reviews)
4 Bedrooms
3 Baths
10 Guests
1797.57 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Parking
£492/Night
7 Nights - £3,442
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
3 Guests
900 ft²
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
£100/Night
7 Nights - £704
House
10.0(5 Reviews)
3 Bedrooms
2 Baths
7 Guests
1463.89 ft²
- View
- Pet Friendly
- Parking
- Air Conditioner
£303/Night
7 Nights - £2,123
House
9.4(32 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£163/Night
7 Nights - £1,138
Why Choose Rent By Owner for your Hampton Roads 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 Hampton Roads
How to Book Your Hampton Roads 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 Hampton Roads
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 Hampton Roads, VA
Tidewater Region
Outer Banks
Dare County
Nags Head
Northern North Carolina Beaches
Norfolk - Virginia Beach
Cape Hatteras National Seashore
Currituck County
Corolla
Hatteras Island
Virginia Beach
Kill Devil Hills
Frequently Asked Questions About Hampton Roads Winter Rentals
1. What are the top 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
- Cozy, Dog-friendly Duplex At The North End Short Walk To The Beach!
- Adorable Cottage In The Heart Of The Old Beach Area, Close To The Boardwalk.
- OCEANFRONT☆One level living w/ramp access to house & dune deck. Walk to dining!
- Breezy, Quaint, and Dog- Friendly North End duplex.
- OCEANFRONT! BOARDWALK TO THE BEACH. COMPLIMENTARY AMENITIES! GUEST FAVORITE!
- HAPPY GUESTS
- Riverfront House, Dock, Hot Tub, Salt Pool, near beach, Free WiFi
- Private 2,000 Sq Ft Cottage in Historic Yorktown- w/trolley access
- Don't miss out on summer. 1 Wk avail 8/29-9/5/26. Great Location&Fido Friendly,
2. How many Winter Rentals are available in Hampton Roads?
Currently, the total number of properties listed by RBO in 2026 is over 16308 in the Hampton Roads area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Hampton Roads.
More Rentals You May Like Near Hampton Roads
House
10.0(5 Reviews)
1 Bedroom
1 Bath
10 Guests
2647.92 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Parking
£289/Night
7 Nights - £2,022
Condo
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
£231/Night
7 Nights - £1,615
Apartment
1 Bedroom
1 Bath
3 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
£224/Night
7 Nights - £1,566
Apartment
1 Bedroom
1 Bath
3 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
£207/Night
7 Nights - £1,452
Condo
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
£207/Night
7 Nights - £1,446
House
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
£112/Night
7 Nights - £784
Boat Rental
10.0(211 Reviews)
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Parking
- Air Conditioner
Internet
£267/Night
7 Nights - £1,873
House
10.0(72 Reviews)
5 Bedrooms
4 Baths
13 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£390/Night
7 Nights - £2,730
House
10.0(65 Reviews)
4 Bedrooms
4 Baths
12 Guests
2600 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£743/Night
7 Nights - £5,199
House
10.0(38 Reviews)
6 Bedrooms
6 Baths
16 Guests
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Pet Friendly
£1,052/Night
7 Nights - £7,367
House
10.0(37 Reviews)
3 Bedrooms
2 Baths
4 Guests
1670 ft²
Private Pool- Fireplace/Heating
- Pool
- Balcony/Terrace
£561/Night
7 Nights - £3,924
Condo
10.0(23 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
£331/Night
7 Nights - £2,319
