Introduction
What to do
Where to eat
When to visit
How to get there
Where to stay
Renting a car

Winchester travel guide

Winchester Tourism | Winchester Guide

You're Going to Love Winchester

With a population of 26.203, Winchester is a must-see destination in Virginia, United States. It is among the most popular tourist destinations in the country. We recommend you stay at least 3 days in order to fully appreciate everything Winchester has to offer.

Where to Eat in Winchester

If you’re looking for affordable options, Village Square Restaurant (103 N Loudoun St) and Uno Pizzeria & Grill – Old Town Winchester (103 E Piccadilly St) are great picks.

When to visit Winchester

Winchester in November
Estimated hotel price
$105
1 night at 3-star hotel
Winchester in November
Estimated hotel price
$105
1 night at 3-star hotel

Looking for warm weather? Then head to Winchester in July, when the average temperature is 75.2 °F, and the highest can go up to 87.8 °F. The coldest month, on the other hand, is January, when it can get as cold as 23 °F, with an average temperature of 32 °F. You’re likely to see more rain in June, when precipitation is around 3.9″. In contrast, February is usually the driest month of the year in Winchester, with an average rainfall of 2.2″.

Data provided by weatherbase
Temperatures
Temperatures
Data provided by weatherbase

How to Get to Winchester

Plane

Although Winchester doesn’t have its own airport, you can fly to Hagerstown Regional (HGR), which is located 69 km from Winchester. The shortest domestic flight to Winchester departs from Atlanta and takes around 1h 45m.

Train

Amtrak is the most popular train carrier serving Winchester, followed by Acela. The train journey from Winchester to Philadelphia takes 1h 55m and costs around $11 for a one-way ticket. When coming by train from Charlottesville, expect to pay about $20 for a 2h 06m trip.

Car

Another option to get to Winchester is to pick up a car rental from Washington, D.C., which is about 102 km from Winchester. You’ll find branches of Turo and Movly, among others, in Washington, D.C..

Bus

Several bus lines operate bus routes to Winchester, including Bus, OurBus and Washington Deluxe. From Richmond, the bus ride to Winchester takes 225 km and will cost you around $30. From Philadelphia, the ticket costs about $24 for a journey of 274 km.

Plane

Although Winchester doesn’t have its own airport, you can fly to Hagerstown Regional (HGR), which is located 69 km from Winchester. The shortest domestic flight to Winchester departs from Atlanta and takes around 1h 45m.

Train

Amtrak is the most popular train carrier serving Winchester, followed by Acela. The train journey from Winchester to Philadelphia takes 1h 55m and costs around $11 for a one-way ticket. When coming by train from Charlottesville, expect to pay about $20 for a 2h 06m trip.

Car

Another option to get to Winchester is to pick up a car rental from Washington, D.C., which is about 102 km from Winchester. You’ll find branches of Turo and Movly, among others, in Washington, D.C..

Bus

Several bus lines operate bus routes to Winchester, including Bus, OurBus and Washington Deluxe. From Richmond, the bus ride to Winchester takes 225 km and will cost you around $30. From Philadelphia, the ticket costs about $24 for a journey of 274 km.

Airports near Winchester

HGRHagerstown Regional
FDKFrederick

Airlines serving Winchester

KLM
Good (1,513 reviews)
British Airways
Good (7,969 reviews)
Delta
Good (8,451 reviews)
Turkish Airlines
Good (4,356 reviews)
Iberia
Good (3,214 reviews)
Air France
Good (1,585 reviews)
United Airlines
Good (9,699 reviews)
Emirates
Excellent (3,571 reviews)
Qatar Airways
Good (3,728 reviews)
Scandinavian Airlines
Good (1,772 reviews)
Air Canada
Good (11,017 reviews)
LOT
Good (1,189 reviews)
Finnair
Good (1,393 reviews)
TAP AIR PORTUGAL
Good (2,250 reviews)
Cathay Pacific
Good (1,326 reviews)
Etihad Airways
Good (1,435 reviews)
Alaska Airlines
Good (12,352 reviews)
JetBlue
Good (2,973 reviews)
Malaysia Airlines
Good (307 reviews)
China Eastern
Good (211 reviews)
Show more

Where to stay in Winchester

If you’re on a budget, well-reviewed accommodations include Microtel Inn & Suites by Wyndham Winchester and Candlewood Suites Winchester By IHG.

Where to stay in popular areas of Winchester

Most booked hotels in Winchester

See all
The George Washington - A Wyndham Grand Hotel
3 stars
Excellent (9.1, 972 reviews)
$125+
View
TownePlace Suites by Marriott Winchester
3 stars
Excellent (9.2, 120 reviews)
$120+
View
Holiday Inn Winchester Se-Historic Gateway By IHG
3 stars
Excellent (8.9, 866 reviews)
$84+
View
La Quinta by Wyndham Winchester
3 stars
Excellent (8.8, 1877 reviews)
$88+
View
Country Inn & Suites by Radisson, Winchester, VA
3 stars
Excellent (8.3, 2109 reviews)
$79+
View
Travelodge by Wyndham Winchester
2 stars
Good (7.8, 2103 reviews)
$64+
View

Renting a car in Winchester

Renting a car in Winchester costs $50 per day, on average, or $151 if you want to rent if for 3 days.

It’s generally cheaper to rent your vehicle outside the airport: locations in the city are around 22% cheaper than airport locations in Winchester.

Expect to pay $4.77 per gallon in Winchester (average price from the past 30 days). Depending on the size of your rental car, filling up the tank will cost between $57.24 and $76.31. The most frequently booked car type in Winchester is Compact (Chevrolet Equinox or similar). If you’re looking to save money, though, keep in mind that Intermediate rental cars (Jeep Cherokee or similar) are, on average, 62% cheaper than other rental car types in the city.

Renting a car in Winchester costs $50 per day, on average, or $151 if you want to rent if for 3 days.

It’s generally cheaper to rent your vehicle outside the airport: locations in the city are around 22% cheaper than airport locations in Winchester.

Expect to pay $4.77 per gallon in Winchester (average price from the past 30 days). Depending on the size of your rental car, filling up the tank will cost between $57.24 and $76.31. The most frequently booked car type in Winchester is Compact (Chevrolet Equinox or similar). If you’re looking to save money, though, keep in mind that Intermediate rental cars (Jeep Cherokee or similar) are, on average, 62% cheaper than other rental car types in the city.

Best car rental deals in Winchester

Economy

2 Adults, 2 Bags

$40/day

Economy

Supplier choice

5 Adults, 5 Bags

$40/day

Supplier choice
Find car rentals in Winchester