$56 Car Rental Windsor, VA

This content is based on real traveler data from Expedia, aggregated using AI to highlight insights that help you plan your trip. Updated: August 13, 2026.

Reasons to book a car rental in and around Windsor

Renting a car in Windsor provides the freedom and flexibility to explore the area at your own pace. This option is particularly appealing for families, couples, or anyone seeking outdoor and cultural experiences. With a rental car, you can easily manage your luggage and travel plans without relying on public transportation. Key attractions such as Lake Prince, located 7 miles from Windsor, offer beautiful scenery and romantic spots. For cultural experiences, visit the Suffolk Center for Cultural Arts, just 11 miles away. You can also explore the historic Boykin's Tavern, located right in Windsor.

Additionally, a car allows you to venture to nearby cities like Suffolk, which features not only Lake Prince and the Suffolk Center for Cultural Arts but also Riddick's Folly House Museum. The city of Isle of Wight, known for Smithfield Historic District and Windsor Castle Park, is easily accessible as well. Zuni, a mere 6 miles away, also has attractions like Boykin's Tavern and Lake Prince. Overall, renting a car enhances your travel experience by giving you the ability to explore the diverse offerings in and around Windsor comfortably.

Where to stay in and around Windsor

• Suffolk: Located 11 miles from Windsor, Suffolk offers a blend of family-friendly and romantic experiences. Visitors can explore attractions like Lake Prince, perfect for outdoor activities and scenic views. The Suffolk Center for Cultural Arts and Riddick's Folly House Museum are excellent for culture enthusiasts. After a day of exploration, enjoy a meal at one of the local restaurants or wineries.
• Isle of Wight: Nestled in the area of Windsor, Isle of Wight is an ideal destination for those seeking outdoor adventures and scenic beach experiences. The Windsor Castle Park is great for family outings and urban exploration. History buffs can visit the Smithfield Historic District and Historic Jamestowne for a cultural deep dive. Local wineries and breweries also offer refreshing options for drinks.
• Smithfield: Located 13 miles from Windsor, Smithfield is known for its outdoor, family, and romantic activities. The Isle of Wight County Museum provides insight into local history, while the Smithfield Historic District offers charming streets to explore. Visitors can unwind at local beaches or enjoy attractions like amusement parks and shopping centers, along with various dining options featuring local wineries.

10 tips to save on your car rental in and around Windsor

1. Use filters to find the right car: Refine your search by selecting specific vehicle types and features. Whether you require an SUV for added space, a convertible for summer enjoyment, or an economy car for cost-effectiveness, utilize the filters on Expedia to discover the ideal option for your journey.
2. Book in advance to help lower costs: Rental rates vary with demand, so it’s advisable to secure your vehicle well ahead of your trip. By booking early, you're more likely to obtain lower prices and enjoy a broader selection, particularly during peak travel seasons.
3. Consider a smaller car for savings: Compact cars are typically more affordable to rent and easier to maneuver in crowded areas. Mid-size rentals strike a good balance between price, comfort, and fuel efficiency.
4. Age guidelines: Drivers under the age of 30 may encounter higher deposits or daily fees, and certain vehicle categories—such as SUVs or luxury models—might not be available. This can also apply to renters over 70 years old. Always verify the age restrictions before making a reservation.
5. Check fuel policies: Some rental agreements require a full-to-full fuel policy, which means you must return the car with a full tank to avoid extra fees. This is generally the best option. Other rentals may offer full-to-empty or prepaid fuel solutions, which can also be convenient. Just ensure you return the vehicle empty in that case.
6. Save on city and airport pickups: Picking up your rental car at the airport often incurs a surcharge, but the added convenience may make it worthwhile.
7. Know your payment options: Most car rental companies exclusively accept credit cards for payment.
8. Understand your insurance coverage: Car rental insurance can help you avoid unnecessary expenses and provides peace of mind in case of unexpected events during your trip. Adding car rental insurance is straightforward when booking through Expedia.
9. Consider unlimited mileage: If you plan on taking long road trips, search for rentals that offer unlimited mileage to prevent additional charges.
10. Bring your driver's license and ID: A valid driver's license is necessary to rent a car.

Finding the cheapest car rentals in Windsor

Using our Search Wizard

If the deals that are available on our page do not suit your needs, then enter Windsor into the search wizard at the top of the page. We will compare all the best deals available for your car rental in Windsor and provide you with a list of the cheapest options, with no added fees.

Renting a car in Windsor

Pay at pickup is available, so you don’t have to worry about spending your money until you arrive at your vehicle in Windsor. We partner with reliable partners that guarantee an enjoyable experience for solo travelers, couples, and families. Package your car with a flight or hotel to unlock even more savings from Expedia.

Expected prices in Windsor

Prices are subject to seasonal change depending on when you decide to arrange your car rental but right now you can book from $56.

Flexibility & Cancellation

Most car suppliers offer penalty-free cancellations, so you don’t have to worry about losing money if your plans change. To cancel your booking log into your account through the Trips portal. Click manage booking and cancel this car. If you needed to alter your booking, then you can create a new one once you have canceled.

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Car classes available from Expedia in 2026

The classes of vehicles available will change depending on your chosen location.

• Compact car rentals    
• Convertible car rentals    
• Economy car rentals    
• Fullsize car rentals    
• Luxury car rentals
• Midsize car rentals    
• Mini car rentals    
• Minivan rentals    
• Pickup car rentals    
• Premium car rentals
• Sportscar rentals    
• Standard car rentals    
• SUV rentals    
• Van rentals