Hampton Roads Winter Rental
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $189/Night
For 7 Nights US $1,324
398.26 ft²
4 Guests
1 Bedroom
1 Bathroom
Bed & Breakfast
- Fireplace/Heating
- View
- Parking
US $232/Night
For 7 Nights US $1,624
US $106/Night
For 7 Nights US $745
1500 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $288/Night
For 7 Nights US $2,013
850.35 ft²
6 Guests
1 Bedroom
2 Bathrooms
Free Cancellation
Bed & Breakfast
- Fireplace/Heating
- View
- Parking
US $318/Night
For 7 Nights US $2,224
1000 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $148/Night
For 7 Nights US $1,036
1797.57 ft²
10 Guests
4 Bedrooms
3 Bathrooms
House
- Hot Tub
- Spa
- Fireplace/Heating
US $657/Night
For 7 Nights US $4,599
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $194/Night
For 7 Nights US $1,356
US $578/Night
For 7 Nights US $4,048
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $410/Night
For 7 Nights US $2,867
2647.92 ft²
10 Guests
1 Bedroom
1 Bathroom
House
- Fireplace/Heating
- View
- Pet Friendly
US $386/Night
For 7 Nights US $2,702
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $231/Night
For 7 Nights US $1,620
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
Norfolk - Virginia Beach
Currituck County
Cape Hatteras National Seashore
Corolla
Hatteras Island
Nags Head
Northern North Carolina Beaches
Virginia Beach
Kinnakeet
Hampton Roads Winter Rental Frequently Asked Questions
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.
- Fantastic home in the heart of the VB Resort Area Walk to Beach, Boardwalk.
- Live like a local in the heart of Nags Head! No cleaning fee/2:00 pm check-in!
- Breezy, Quaint, and Dog- Friendly North End duplex.
- Carolina Cottage-Family friendly cottage in the Outer Banks-Community Pool
- OCEANFRONT! BOARDWALK TO THE BEACH. COMPLIMENTARY AMENITIES! GUEST FAVORITE!
- HAPPY PEOPLE ONLY! SEMI-OCEANFRNT SEA VIEW/POOL/HOT TUB/2 MIN WALK TO BCH
- Riverfront House, Dock, Hot Tub, Salt Pool, near beach, Free WiFi
2. How many Winter Rentals are available in Hampton Roads?
Currently, the total number of properties listed by RBO in 2026 is over 16157 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
645.83 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
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- Oceanfront
- Hot Tub
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- Oceanfront
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1100 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
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- Fireplace/Heating
- Balcony/Terrace
- Kitchen
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900 ft²
7 Guests
2 Bedrooms
1 Bathroom
Family Friendly
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- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
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1200 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
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- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
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For 7 Nights US $1,451
6 Guests
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- Hot Tub
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4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $250/Night
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6 Guests
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Ocean View
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- Oceanfront
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- Fireplace/Heating
US $188/Night
For 7 Nights US $1,314
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- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
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For 7 Nights US $676
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- Hot Tub
- Fireplace/Heating
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1 Bathroom
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- Oceanfront
- Hot Tub
- Fireplace/Heating
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