Winter Rentals in Ware:【 GREAT PRICES 】Rent By Owner

Ware Winter Rental

Highly Rated

Cottage

Historic Cottage on Ware River Estate

10.0

Exceptional

(279 Reviews)

1 Bedroom 1 Bath 4 Guests

R3,027/Night 7 Nights - R21,188

View Deal

RV Rental

Chesapeake Bay RV Resort Thousand Trails - Campground

8.6

Fabulous

(25 Reviews)

1 Bedroom 1 Bath

R2,549/Night 7 Nights - R17,843

View Deal

Relax, Refresh, Renew.Waterfront Cottage.Near Williamsburg

Highly Rated

Cottage

Relax, Refresh, Renew.Waterfront Cottage.Near Williamsburg

10.0

Exceptional

(184 Reviews)

2 Bedrooms 2 Baths 4 Guests 1500 ft²

R4,969/Night 7 Nights - R34,794

View Deal

"Bee Haven" Cottage Retreat Near Colonial Williamsburg

Highly Rated

House

"Bee Haven" Cottage Retreat Near Colonial Williamsburg

10.0

Exceptional

(112 Reviews)

2 Bedrooms 1 Bath 4 Guests 1000 ft²

R2,324/Night 7 Nights - R16,268

View Deal

Waterfront with Private Pier and Tranquil Water views!

Price Dropped

Cottage

Waterfront with Private Pier and Tranquil Water views!

10.0

Exceptional

(108 Reviews)

2 Bedrooms 1 Bath 4 Guests 1300 ft²

R4,001/Night 7 Nights - R28,007

View Deal

Cottage

Relaxing Riverfront Cottage w/Boat Dock!

9.8

Exceptional

(46 Reviews)

2 Bedrooms 1 Bath 4 Guests 616 ft²

R4,137/Night 7 Nights - R28,965

View Deal

Cottage

Bee Humble Cottage w/in 20mins to Public Beaches

9.8

Exceptional

(31 Reviews)

2 Bedrooms 1 Bath 4 Guests 1100 ft²

R2,318/Night 7 Nights - R16,220

View Deal

Family-Friendly Main St Gloucester Apt w/Balcony!

Price Dropped

Apartment

Family-Friendly Main St Gloucester Apt w/Balcony!

9.8

Exceptional

(6 Reviews)

2 Bedrooms 1 Bath 7 Guests 900 ft²

R3,708/Night 7 Nights - R25,961

View Deal

House

Radiant Gloucester House w/Private Porch!

9.4

Exceptional

(32 Reviews)

2 Bedrooms 1 Bath 6 Guests 1200 ft²

R3,778/Night 7 Nights - R26,448

View Deal

Highly Rated

House

Welcome to "The Happy Soul"

10.0

Exceptional

(58 Reviews)

3 Bedrooms 2 Baths 6 Guests 1800 ft²

R3,524/Night 7 Nights - R24,662

View Deal

A Sandy White Beach Retreat * NEAR WILLIAMSBURG*

Highly Rated

House

A Sandy White Beach Retreat * NEAR WILLIAMSBURG*

9.8

Exceptional

(157 Reviews)

3 Bedrooms 2 Baths 6 Guests 1450 ft²

R5,486/Night 7 Nights - R38,398

View Deal

The River House Getaway! Come Relax and Enjoy!

Highly Rated

House

The River House Getaway! Come Relax and Enjoy!

9.8

Exceptional

(148 Reviews)

3 Bedrooms 2 Baths 8 Guests 2000 ft²

R3,129/Night 7 Nights - R21,902

View Deal

More Top-Rated Winter Rental in Ware Area

Why Choose Rent By Owner for your Ware 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.

Best Times to Visit Ware

When should you plan your Winter Rental stay?

Finding the ideal time to enjoy winter rentals here can enhance your experience, as seasonal conditions and local events in Gloucester influence the region’s charm during different parts of the year, making planning ahead essential for a seamless getaway.

Peak Season Highlights

Late Spring to Early Summer (May - June)

During this period, you can enjoy the region's vibrant atmosphere as nature begins to bloom, making it an ideal time for outdoor activities and exploring local scenery.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F

Early Fall (September - October)

This time of year offers comfortable weather with beautiful fall foliage, perfect for experiencing the area's scenic views and engaging in seasonal outdoor pursuits.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F

Off-Season Highlights

Winter (December - February)

The winter months bring cooler temperatures, creating a cozy setting for your winter rentals while allowing you to enjoy quiet moments away from peak crowds.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F

Mid to Late Fall (November)

As the region transitions into winter, you’ll find fewer visitors, providing a peaceful environment to relax and unwind during your stay.

Average Temperature Daytime: 55°F to 65°F - Nighttime: 40°F to 50°F

Weekly Weather Forecast for Ware

How to Book Your Ware 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

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Ware

More Top-Rated Winter Rental in Ware Area

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

Outdoor Amenities

Enjoy the outdoors with access to spacious private gardens or yards for relaxing or family activities.
Make the most of the region's scenic views with outdoor seating areas, perfect for morning coffees or evening sunsets.
Take advantage of outdoor grilling facilities to prepare delicious meals while enjoying the fresh air.
Stay active with nearby walking trails or nature paths that showcase the area's natural beauty.
Utilize outdoor fire pits or fireplaces for cozy gatherings during chilly winter evenings.
Benefit from available boat docks or access to waterfront areas if your rental is near the water.
Use outdoor recreational equipment such as kayaks or paddleboards to explore the local waterways and preserve the tranquil surroundings.

Top Attractions Around Ware

What attractions are nearby?

During your stay here, you can enjoy a variety of outdoor activities and local attractions that highlight the charm of Ware, Gloucester, making it an ideal destination for exploring nearby parks, historical sites, and scenic waterways in this welcoming region.

Family Activities

Ware River Trail Embark on a family-friendly hike along this scenic trail that offers picturesque views and easy access to nature during your winter stay in the region.
Gloucester Point Park Spend quality time at this charming park featuring open spaces, playgrounds, and waterfront views, ideal for outdoor fun with children.
Historic Ware House Explore this local historic site to learn about the area's rich past, providing educational entertainment for the whole family.
Fishing at Beaverdam Park Enjoy a relaxing day of fishing at this peaceful spot that welcomes families looking to unwind by the water during their winter visit.

Adult Activities

Boating and Fishing: Enjoy the tranquil waters by taking part in boating or fishing activities, which are popular ways to relax and explore the scenic surroundings here.
Historical Tours: Discover the rich history of this region through guided tours and visits to local landmarks that showcase its cultural heritage.
Golfing: Spend your days on well-maintained golf courses that offer a perfect setting for both beginners and seasoned players to enjoy a round during your stay.
Wildlife Watching: Experience the diverse native wildlife by exploring nearby nature reserves and parks, ideal for observing local flora and fauna in their natural habitat.

Other Places to Stay in Ware, VA

North

Explore 80 Properties

Schley

Explore 67 Properties

Ware Neck

Explore 62 Properties

Zanoni

Explore 44 Properties

Gloucester Museum of History

Explore 42 Properties

Riverside Walter Reed Hospital

Explore 41 Properties

Petsworth

Explore 37 Properties

Gloucester

Explore 37 Properties

Gloucester County

Explore 36 Properties

Ark

Explore 30 Properties

More Places to Stay Near Ware

Ware Travel Tips

How Can You Make the Most of Your Stay?

Plan Ahead Book your winter rentals early to secure the best accommodations and take advantage of seasonal discounts in this charming region.
Explore Local Cuisine Enjoy local dining options to get a taste of the area's unique flavors, enhancing your stay in Ware and its surroundings.
Dress Appropriately Prepare for the winter climate by packing layered clothing to stay comfortable while exploring outdoor attractions here.
Discover Hidden Gems Take time to explore lesser-known spots in the area to experience the region’s authentic character beyond popular destinations.

Transportation Options

Personal Vehicles: Driving your own car offers the most convenience for exploring the area and accessing your winter rental with flexibility during your stay.
Taxi Services: Local taxi providers provide reliable point-to-point transportation, ideal for quick trips or traveling without the hassle of parking.
Ride-Sharing Options: Ride-sharing platforms are widely available here, offering affordable and efficient transportation directly to your winter rental.
Public Transportation: Although limited, regional bus services can be a budget-friendly way to navigate the vicinity of Ware and nearby attractions in the region.

Local Customs Options

Southern Hospitality Visitors often experience the welcoming and friendly attitude characteristic of this area, reflecting its warm community spirit.
Local Seafood Traditions The region boasts a rich tradition of seafood, especially Chesapeake Bay oysters and crabs, which are integral to local dining customs.
Historic Preservation Respect for history is evident through the preservation of historic buildings and sites that tell the story of the area's colonial and maritime past.
Community Events Engaging in year-round local festivals and outdoor gatherings provides insight into the area's vibrant cultural life and community values.

Frequently Asked Questions About Ware Winter Rentals

1. What are the top Winter Rentals in Ware?

There are a lot of options in Ware. If you plan on staying in the Ware area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Winter Rentals in Ware:

2. How many Winter Rentals are available in Ware?

Currently, the total number of properties listed by RBO in 2026 is over 30 in the Ware area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Ware. 

3. What is the cancellation policy for winter rentals in Ware, Gloucester, Virginia?

To understand the specific cancellation policy for your chosen winter rental, please review the listing details or contact the property owner directly. Policies may vary depending on the individual property and booking terms.

4. Are there any additional fees I should be aware of when booking winter accommodations in this area?

Additional fees such as cleaning, service charges, or taxes are often outlined in the listing. For clarity on all costs involved, refer to the detailed property description or reach out to the host before completing your reservation.

5. How do I ensure my booking is secure and confirmed?

All reservations are managed through a secure platform that verifies bookings once payment is processed. To confirm your stay, review the confirmation details provided after booking and contact the host if needed.

6. What amenities are typically included in winter rentals here during the season?

Amenities can vary by property but often include heating, fireplaces, and other features suitable for winter stays. For exact details, consult the property's listing or contact the owner directly.

7. Can I modify or cancel my reservation if plans change?

Modifications or cancellations depend on the policies set by the individual property owner. Check the listing's cancellation and modification terms or contact the host for assistance with your reservation.