Why Choose Rent By Owner for your Hampton Roads Winter Rental?
What makes our Winter Rental special?
Weekly Weather Forecast for Hampton Roads
How to Book Your Hampton Roads Winter Rental
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Hampton Roads
Common Winter Rental Amenities
What amenities can you expect?
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.

























