Ware Winter Rental

Cottage
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like-icon10.0
Exceptional
(287 Reviews)
1 Bedroom 1 Bath 4 Guests
  • Parking
    Parking
  • Ocean View
    Ocean View
More amenities
US $230/Night 7 Nights - US $1,609
RV Rental
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Fabulous
(25 Reviews)
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  • Oceanfront
    Oceanfront
  • Hot Tub
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US $157/Night 7 Nights - US $1,099
Cottage
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like-icon10.0
Exceptional
(188 Reviews)
2 Bedrooms 2 Baths 4 Guests 1500 ft²
  • Hot Tub
    Hot Tub
  • Parking
    Parking
More amenities
US $339/Night 7 Nights - US $2,372
House
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like-icon10.0
Exceptional
(116 Reviews)
2 Bedrooms 1 Bath 4 Guests 1000 ft²
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $190/Night 7 Nights - US $1,328
Cottage
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like-icon10.0
Exceptional
(111 Reviews)
2 Bedrooms 1 Bath 4 Guests 1300 ft²
  • Parking
    Parking
  • Ocean View
    Ocean View
More amenities
US $350/Night 7 Nights - US $2,449
Cottage
Map-icon
like-icon9.8
Exceptional
(33 Reviews)
2 Bedrooms 1 Bath 4 Guests 1100 ft²
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $211/Night 7 Nights - US $1,476
Apartment
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like-icon9.8
Exceptional
(7 Reviews)
2 Bedrooms 1 Bath 7 Guests 900 ft²
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $333/Night 7 Nights - US $2,333
House
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like-icon9.4
Exceptional
(32 Reviews)
2 Bedrooms 1 Bath 6 Guests 1200 ft²
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $217/Night 7 Nights - US $1,520
New
Cottage
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like-icon9.8
Exceptional
(48 Reviews)
2 Bedrooms 1 Bath 4 Guests 616 ft²
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $279/Night 7 Nights - US $1,954
House
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like-icon10.0
Exceptional
(58 Reviews)
3 Bedrooms 2 Baths 6 Guests 1800 ft²
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $217/Night 7 Nights - US $1,519
House
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like-icon9.4
Exceptional
(13 Reviews)
4 Bedrooms 3 Baths 8 Guests
  • Parking
    Parking
  • Ocean View
    Ocean View
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US $686/Night 7 Nights - US $4,804
House
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like-icon10.0
Exceptional
(25 Reviews)
2 Bedrooms 1 Bath 5 Guests 1250 ft²
  • Hot Tub
    Hot Tub
  • Parking
    Parking
More amenities
US $412/Night 7 Nights - US $2,884

Discover & compare premier experiences around Gloucester

We understand the importance of quality and reliability in your travel experiences. That's why we've curated options from the most reputable tour and activity providers globally, ensuring you have access to top-tier adventures.

Why Choose Rent By Owner for your Ware Winter Rental?

What makes our Winter Rental special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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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

summer
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
autumn
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

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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
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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

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.

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.
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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.
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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

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.

Ware Winter Rental Frequently Asked Questions

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 29 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.

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