Condo
10.0(356 Reviews)
2 Bedrooms
1 Bath
6 Guests
950 ft²
Oceanfront
Parking
Ocean View
Balcony/Terrace
£199/Night
7 Nights - £1,392
Hampton Roads Winter Rental
10.0
Bed & Breakfast
10.0(11 Reviews)
1 Bedroom
1 Bath
4 Guests
398.26 ft²
EV Charge Station- Parking
View
Air Conditioner
£170/Night
7 Nights - £1,190
Bed & Breakfast
10.0(72 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
- Balcony/Terrace
Kitchen
£180/Night
7 Nights - £1,261
Condo
10.0(279 Reviews)
2 Bedrooms
1 Bath
6 Guests
950 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
£236/Night
7 Nights - £1,654
Bed & Breakfast
10.0(8 Reviews)
1 Bedroom
2 Baths
6 Guests
850.35 ft²
- EV Charge Station
- Parking
- View
- Air Conditioner
£233/Night
7 Nights - £1,629
Boat Rental
10.0(213 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
Internet
£256/Night
7 Nights - £1,796
House
10.0(7 Reviews)
4 Bedrooms
4 Baths
8 Guests
1797.57 ft²
- Oceanfront
- Parking
Pool- Ocean View
£424/Night
7 Nights - £2,966
Condo
10.0(187 Reviews)
2 Bedrooms
2 Baths
6 Guests
1000 ft²
Private Pool- Oceanfront
- Parking
- Pool
£349/Night
7 Nights - £2,446
House
10.0(6 Reviews)
1 Bedroom
1 Bath
10 Guests
2647.92 ft²
- Parking
- View
- Air Conditioner
- Internet
£283/Night
7 Nights - £1,980
Condo
10.0(185 Reviews)
2 Bedrooms
2 Baths
6 Guests
1000 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
£121/Night
7 Nights - £846
House
10.0(5 Reviews)
4 Bedrooms
3 Baths
10 Guests
1797.57 ft²
Hot Tub- Parking
Spa- Internet
£481/Night
7 Nights - £3,369
House
10.0(178 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
£176/Night
7 Nights - £1,229
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.
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
Norfolk - Virginia Beach
Cape Hatteras National Seashore
Currituck County
Corolla
Hatteras Island
Nags Head
Northern North Carolina Beaches
Virginia Beach
Kinnakeet
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
- Fantastic home in the heart of the VB Resort Area Walk to Beach, Boardwalk.
- Historic Cottage on Ware River Estate
- Riverfront House, Dock, Hot Tub, Salt Pool, near beach, Free WiFi
- 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]
- Ivey Coast 6BR, Sleeps 14,Pool,Hot Tub, pool table, arcade, 2 min walk to Ocean
- Nags Head 2 blocks to beach, 3bdrms. Booking for late summer & fall. 5⭐reviews
- Relax, Rejuvenate, and Refresh
- 321 Packed with Amenities and Close to the Beach!
2. How many Winter Rentals are available in Hampton Roads?
Currently, the total number of properties listed by RBO in 2026 is over 16165 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)
3 Bedrooms
2 Baths
7 Guests
1463.89 ft²
- Parking
- View
- Air Conditioner
- Internet
£297/Night
7 Nights - £2,078
Condo
10.0(178 Reviews)
1 Bedroom
1 Bath
2 Guests
900 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
£163/Night
7 Nights - £1,139
New
Condo
10.0(161 Reviews)
1 Bedroom
1 Bath
3 Guests
756 ft²
- Hot Tub
- Parking
- Pool
- Kitchen
£260/Night
7 Nights - £1,818
Condo
10.0(152 Reviews)
2 Bedrooms
2 Baths
6 Guests
1000 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
£311/Night
7 Nights - £2,176
House
10.0(143 Reviews)
1 Bedroom
1 Bath
2 Guests
1000 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
£190/Night
7 Nights - £1,331
House
10.0(133 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
£157/Night
7 Nights - £1,100
Condo
10.0(118 Reviews)
2 Bedrooms
3 Baths
4 Guests
1500 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
£425/Night
7 Nights - £2,972
Cottage
10.0(117 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
£200/Night
7 Nights - £1,402
Cottage
10.0(109 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
£201/Night
7 Nights - £1,405
Condo
10.0(102 Reviews)
1 Bedroom
2 Baths
4 Guests
700 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
£225/Night
7 Nights - £1,576
House
10.0(98 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
£647/Night
7 Nights - £4,531
Condo
10.0(94 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
£310/Night
7 Nights - £2,168
