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
$91
1 night at 3-star hotel
Winchester in January
Estimated hotel price
$91
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 Atlanta and takes around 1h 40m.

Train

Amtrak is the most popular train carrier serving Winchester, followed by Lufthansa. The train journey from Winchester to Baltimore takes 0h 47m and costs around $6 for a one-way ticket. When coming by train from Philadelphia, expect to pay about $11 for a 1h 56m 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 Sixt, 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 140 miles and will cost you around $50. From New York, the ticket costs about $58 for a journey of 210 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 Atlanta and takes around 1h 40m.

Train

Amtrak is the most popular train carrier serving Winchester, followed by Lufthansa. The train journey from Winchester to Baltimore takes 0h 47m and costs around $6 for a one-way ticket. When coming by train from Philadelphia, expect to pay about $11 for a 1h 56m 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 Sixt, 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 140 miles and will cost you around $50. From New York, the ticket costs about $58 for a journey of 210 miles.

Airports near Winchester

HGRHagerstown Regional
FDKFrederick

Airlines serving Winchester

KLM
Good (1,428 reviews)
Delta
Good (8,018 reviews)
British Airways
Good (7,595 reviews)
Turkish Airlines
Good (4,106 reviews)
United Airlines
Good (9,097 reviews)
Qatar Airways
Good (3,687 reviews)
Iberia
Good (3,055 reviews)
Emirates
Excellent (3,440 reviews)
Air France
Good (1,509 reviews)
Air Canada
Good (10,547 reviews)
Etihad Airways
Good (1,335 reviews)
Cathay Pacific
Good (1,099 reviews)
Scandinavian Airlines
Good (1,617 reviews)
Finnair
Good (1,339 reviews)
Alaska Airlines
Excellent (11,484 reviews)
LOT
Good (1,150 reviews)
Malaysia Airlines
Good (283 reviews)
JetBlue
Good (2,896 reviews)
TAP AIR PORTUGAL
Good (2,092 reviews)
Frontier
Okay (3,081 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, 941 reviews)
$114+
View
Holiday Inn Winchester Se-Historic Gateway By IHG
3 stars
Excellent (8.8, 848 reviews)
$64+
View
Spark by Hilton Winchester
3 stars
Excellent (8.8, 484 reviews)
$90+
View
La Quinta by Wyndham Winchester
3 stars
Excellent (8.7, 1733 reviews)
$79+
View
Country Inn & Suites by Radisson, Winchester, VA
3 stars
Excellent (8.2, 2027 reviews)
$72+
View
Travelodge by Wyndham Winchester
2 stars
Good (7.8, 1970 reviews)
$64+
View

Renting a car in Winchester

Renting a car in Winchester costs $49 per day, on average, or $148 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 20% cheaper than airport locations in Winchester.

Expect to pay $3.29 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 $39.52 and $52.69. 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, 59% cheaper than other rental car types in the city.

Renting a car in Winchester costs $49 per day, on average, or $148 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 20% cheaper than airport locations in Winchester.

Expect to pay $3.29 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 $39.52 and $52.69. 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, 59% cheaper than other rental car types in the city.

Best car rental deals in Winchester

Intermediate

5 Adults, 3 Bags

$40/day

Intermediate

Compact SUV

4 Adults, 2 Bags

$44/day

Compact SUV
Find car rentals in Winchester