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 January
Estimated hotel price
$90
1 night at 3-star hotel
Winchester in January
Estimated hotel price
$90
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 43 miles from Winchester. The shortest domestic flight to Winchester departs from Tampa and takes around 2h 15m.

Train

Amtrak is the most popular train carrier serving Winchester, followed by Acela. The train journey from Winchester to Philadelphia takes 1h 59m and costs around $11 for a one-way ticket. When coming by train from Newark, expect to pay about $22 for a 3h 05m trip.

Car

Another option to get to Winchester is to pick up a car rental from Washington, D.C., which is about 64 miles from Winchester. You’ll find branches of Turo and Dollar, among others, in Washington, D.C..

Bus

Several bus lines operate bus routes to Winchester, including Peter Pan Bus Lines, Bus and OurBus. From Philadelphia, the bus ride to Winchester takes 180 miles and will cost you around $13. From Charlottesville, the ticket costs about $53 for a journey of 185 miles.

Plane

Although Winchester doesn’t have its own airport, you can fly to Hagerstown Regional (HGR), which is located 43 miles from Winchester. The shortest domestic flight to Winchester departs from Tampa and takes around 2h 15m.

Train

Amtrak is the most popular train carrier serving Winchester, followed by Acela. The train journey from Winchester to Philadelphia takes 1h 59m and costs around $11 for a one-way ticket. When coming by train from Newark, expect to pay about $22 for a 3h 05m trip.

Car

Another option to get to Winchester is to pick up a car rental from Washington, D.C., which is about 64 miles from Winchester. You’ll find branches of Turo and Dollar, among others, in Washington, D.C..

Bus

Several bus lines operate bus routes to Winchester, including Peter Pan Bus Lines, Bus and OurBus. From Philadelphia, the bus ride to Winchester takes 180 miles and will cost you around $13. From Charlottesville, the ticket costs about $53 for a journey of 185 miles.

Airports near Winchester

HGRHagerstown Regional
FDKFrederick

Airlines serving Winchester

KLM
Good (1,430 reviews)
Delta
Good (8,013 reviews)
British Airways
Good (7,564 reviews)
Turkish Airlines
Good (4,082 reviews)
United Airlines
Good (9,073 reviews)
Iberia
Good (3,040 reviews)
Qatar Airways
Good (3,676 reviews)
Emirates
Excellent (3,429 reviews)
Air France
Good (1,502 reviews)
Air Canada
Good (10,512 reviews)
Etihad Airways
Good (1,330 reviews)
Scandinavian Airlines
Good (1,596 reviews)
Cathay Pacific
Good (1,085 reviews)
Finnair
Good (1,334 reviews)
LOT
Good (1,143 reviews)
Alaska Airlines
Excellent (11,408 reviews)
TAP AIR PORTUGAL
Good (2,082 reviews)
Malaysia Airlines
Good (281 reviews)
JetBlue
Good (2,897 reviews)
Frontier
Okay (3,089 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, 941 reviews)
$114+
View
Holiday Inn Winchester Se-Historic Gateway By IHG
3 stars
Excellent (8.8, 847 reviews)
$73+
View
La Quinta by Wyndham Winchester
3 stars
Excellent (8.7, 1726 reviews)
$82+
View
Microtel Inn & Suites by Wyndham Winchester
2 stars
Excellent (8.7, 627 reviews)
$66+
View
Country Inn & Suites by Radisson, Winchester, VA
3 stars
Excellent (8.2, 2023 reviews)
$73+
View
Travelodge by Wyndham Winchester
2 stars
Good (7.8, 1969 reviews)
$63+
View

Renting a car in Winchester

Renting a car in Winchester costs $50 per day, on average, or $150 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 14% cheaper than airport locations in Winchester.

Expect to pay $3.41 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 $40.88 and $54.51. 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, 58% cheaper than other rental car types in the city.

Renting a car in Winchester costs $50 per day, on average, or $150 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 14% cheaper than airport locations in Winchester.

Expect to pay $3.41 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 $40.88 and $54.51. 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, 58% cheaper than other rental car types in the city.

Car rental agencies in Winchester

Hertz

Hertz
Find car rentals in Winchester