EN
No booking fees. Free cancellation on most cars
Save by finding great deals and securing low price rentals
Compare car rental prices from top suppliers in Winchester with Road Genius. From affordable cars to luxury SUVs and minivans, you'll find vehicles at low prices in convenient locations. Book early for fall foliage and apple blossom season to secure the ride you want and enjoy cruising Skyline Drive, Shenandoah National Park and nearby Civil War sites on your own schedule.
| Location | Pros | Cons |
|---|---|---|
| Winchester Town Center | • Lower rates than major cities • No airport surcharges • Convenient to downtown attractions • Close to hotels and I-81 |
• Limited hours (often 8 AM-6 PM weekdays, shorter on weekends) • Smaller vehicle selection • May be closed Sundays • Limited specialty vehicles |
| Apple Blossom Mall Area | • Near shopping and dining • Multiple rental agencies • Often open Saturdays |
• Limited selection • Transportation needed if arriving by bus • No after-hours pickup |
| Route 50/522 Corridor | • Easy access to highways • Near chain hotels • More parking space |
• Not walkable to downtown • Limited weekend hours • Fewer luxury options |
On average, car rentals in Winchester (VA) cost around $79 per day, with the lowest-priced rentals starting at $36 per day.
Shop around: Compare quotes for Winchester Town Center, Apple Blossom Mall and Route 50/522. Town Center usually wins on price but check hours and vehicle stock.
Time it right: Rates jump during apple blossom (Apr-May) and foliage (Sep-Oct) weekends. Book 3-4 weeks ahead for those windows, but in winter or midsummer you can often score last-minute deals.
Pick the right length: Staying 5+ days? A weekly rate often beats 4-5 separate daily charges. Short trip? Run both options in the search box and pick the cheaper total.
Skip the oversized ride: A compact or midsize handles Skyline Drive just fine and rents for less than an SUV. Upgrade only if you really need the cargo room.
Refuel smart: Top off at stations on Berryville Ave or Pleasant Valley Rd before drop-off to dodge the $9-10/gal refill hit.
Avoid one-way surprises: Returning in another state can add $50-300. If your plan is flexible, compare round-trip vs one-way totals and see if the savings justify looping back to Winchester.
| Area | Type | Hours | Cost | Notes |
|---|---|---|---|---|
| Old Town Winchester | Street parking | Varies | Free (time limits apply) | 2-3 hour limits in most areas; enforced Mon-Fri 8 AM-5 PM |
| Old Town Winchester | Public garages/lots | 24/7 | Free | Loudoun Street, Braddock Street and Court Square autoparks |
| Apple Blossom Mall | Mall parking | Mall hours | Free | Plenty of spaces throughout the property |
| Walmart/Shopping Centers | Lots | Center hours | Free | Large lots along Pleasant Valley Road |
| Jim Barnett Park | Park parking | Park hours | Free | Several lots throughout recreational facility |
Speed limits: 25 mph in downtown/residential areas, 35-45 mph on main roads, 55-70 mph on highways
Key regulations:
Book a car rental so you can visit:
Skyline Drive North Entrance – Shenandoah National Park, overlooks
Harpers Ferry – rivers confluence, National Historical Park
Gettysburg – Civil War battlefield, museum
Luray Caverns – cave network, Car and Carriage Caravan Museum
What documents do I need to rent a car in Winchester?
You'll need to show a valid driver's license, a major credit card in your name and proof of insurance if you don't buy the rental company's coverage. If you are visiting from another country, you should also bring your passport and an International Driving Permit if your license isn't in English.
Is an SUV necessary for visiting Skyline Drive and Shenandoah National Park?
You don't need an SUV, but many people like one for the higher seats and extra room for luggage. Any regular, well-maintained car can handle Skyline Drive in good weather. From December to March, an SUV with all-wheel drive can be helpful. The mountains sometimes get snow and ice and parts of Skyline Drive may close during winter storms.
Where are the best places to refuel before returning my rental?
You can find many gas stations in Winchester, especially along Berryville Avenue (Route 7), Pleasant Valley Road and near the I-81 exits. If you're dropping off your car near I-81 Exit 313 (Millwood Pike), the gas stations there are a good choice. For the cheapest gas, you can check the pumps on Berryville Avenue east of downtown or near the Walmart on Pleasant Valley Road.
How does seasonal tourism affect rental car availability in Winchester?
The fall foliage season from late September to October is the busiest time for car rentals, especially for SUVs and larger cars. The Apple Blossom Festival in late April and early May is also a very busy period. You should book your car far ahead of time for these events. In the winter, you'll usually find more cars available at lower prices.
Are there any toll roads around Winchester?
You won't find any toll roads right in the Winchester area. If you drive toward Washington, D.C. on I-66, you'll pay changing toll prices inside the Beltway during busy times. You'll also pay tolls on the Dulles Toll Road and Dulles Greenway if you drive toward Dulles International Airport. You should ask your rental company how to pay for tolls, like using a transponder or having them bill your license plate.
What should I know about driving in Old Town Winchester?
You should know that cars are not allowed on the Loudoun Street Pedestrian Mall in Old Town. Many nearby streets are one-way, so you need to watch the signs carefully. You can park in public garages (on Braddock Street, Court Square, Loudoun Street and others) or on the street. They charge small fees. Usually, the first hour is free and then it's about $1 per hour during weekday business hours. Traffic is light unless there is a festival or special event.
Is it easy to find parking at trailheads and outdoor recreation areas?
Parking lots at trailheads in Shenandoah National Park often fill up by mid-morning on busy weekends. You should try to arrive before 9 AM or visit on a weekday. Smaller local places like Jim Barnett Park usually have plenty of parking all year. State parks in the area usually have parking spots available, except on holiday weekends.
How far in advance should I book a rental car for visiting during apple harvest season?
If you are visiting during the main apple season (mid-September through October), you should book a car at least 3 to 4 weeks early. People also visit to see the fall leaves at the same time, so all the rental cars in Winchester can get booked on busy weekends. If you want a specific type of car, like an SUV, it's a good idea to book it 4 to 6 weeks ahead of time.
Popular Countries
24/7 Support