Hampton Roads Winter Rental
Cottage
10.0(287 Reviews)
1 Bedroom
1 Bath
4 Guests
Fireplace/Heating
Ocean View
Balcony/Terrace
View
AU $328/Night
7 Nights - AU $2,293
Bed & Breakfast
10.0(10 Reviews)
1 Bedroom
1 Bath
4 Guests
398.26 ft²
- Fireplace/Heating
- View
Parking
Air Conditioner
AU $335/Night
7 Nights - AU $2,344
Bed & Breakfast
10.0(215 Reviews)
1 Bedroom
1 Bath
Spa
Pool- Balcony/Terrace
Breakfast
AU $383/Night
7 Nights - AU $2,678
Cottage
10.0(188 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
Kitchen
AU $492/Night
7 Nights - AU $3,446
Bed & Breakfast
10.0(8 Reviews)
1 Bedroom
2 Baths
6 Guests
850.35 ft²
- Fireplace/Heating
- View
- Parking
- Air Conditioner
AU $458/Night
7 Nights - AU $3,210
House
10.0(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
AU $591/Night
7 Nights - AU $4,138
House
10.0(7 Reviews)
4 Bedrooms
4 Baths
8 Guests
1797.57 ft²
Oceanfront- Fireplace/Heating
- Pool
- Ocean View
AU $835/Night
7 Nights - AU $5,842
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
3 Guests
900 ft²
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
AU $194/Night
7 Nights - AU $1,357
House
10.0(5 Reviews)
4 Bedrooms
3 Baths
10 Guests
1797.57 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Parking
AU $948/Night
7 Nights - AU $6,637
Apartment
9.8(7 Reviews)
2 Bedrooms
1 Bath
7 Guests
900 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
AU $463/Night
7 Nights - AU $3,243
House
10.0(5 Reviews)
3 Bedrooms
2 Baths
7 Guests
1463.89 ft²
- View
- Pet Friendly
- Parking
- Air Conditioner
AU $585/Night
7 Nights - AU $4,093
House
9.4(32 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $313/Night
7 Nights - AU $2,194
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
Hatteras Island
Currituck County
Corolla
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
- 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!
- Carolina Cottage-Family friendly cottage in the Outer Banks-Community Pool
- Breezy, Quaint, and Dog- Friendly North End duplex.
- 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 16462 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
AU $557/Night
7 Nights - AU $3,899
Condo
9.4(8 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
AU $476/Night
7 Nights - AU $3,332
Condo
9.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
AU $306/Night
7 Nights - AU $2,143
Apartment
8.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $153/Night
7 Nights - AU $1,069
Apartment
1 Bedroom
1 Bath
3 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
AU $400/Night
7 Nights - AU $2,800
Condo
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
AU $345/Night
7 Nights - AU $2,416
Condo
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
AU $303/Night
7 Nights - AU $2,123
Apartment
1 Bedroom
1 Bath
3 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
AU $286/Night
7 Nights - AU $2,003
House
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
AU $216/Night
7 Nights - AU $1,512
New
Boat Rental
10.0(212 Reviews)
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Parking
- Air Conditioner
Internet
AU $535/Night
7 Nights - AU $3,742
House
10.0(51 Reviews)
3 Bedrooms
3 Baths
9 Guests
2450 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
AU $776/Night
7 Nights - AU $5,433
House
10.0(47 Reviews)
8 Bedrooms
8 Baths
18 Guests
4050 ft²
Private Pool- Oceanfront
- Hot Tub
- Fireplace/Heating
AU $1,118/Night
7 Nights - AU $7,825
