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 February
Estimated hotel price
$97
1 night at 3-star hotel
Winchester in February
Estimated hotel price
$97
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 45m.

Train

Amtrak is the most popular train carrier serving Winchester, followed by Acela. The train journey from Winchester to Baltimore takes 0h 32m and costs around $6 for a one-way ticket. When coming by train from Philadelphia, expect to pay about $11 for a 1h 57m 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 Movly, among others, in Washington, D.C..

Bus

Several bus lines operate bus routes to Winchester, including OurBus, Washington Deluxe and Peter Pan Bus Lines. From Philadelphia, the bus ride to Winchester takes 140 miles and will cost you around $25. From Charlottesville, the ticket costs about $49 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 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 Baltimore takes 0h 32m and costs around $6 for a one-way ticket. When coming by train from Philadelphia, expect to pay about $11 for a 1h 57m 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 Movly, among others, in Washington, D.C..

Bus

Several bus lines operate bus routes to Winchester, including OurBus, Washington Deluxe and Peter Pan Bus Lines. From Philadelphia, the bus ride to Winchester takes 140 miles and will cost you around $25. From Charlottesville, the ticket costs about $49 for a journey of 185 miles.

Airports near Winchester

HGRHagerstown Regional
FDKFrederick

Airlines serving Winchester

KLM
Good (1,457 reviews)
British Airways
Good (7,757 reviews)
Delta
Good (8,240 reviews)
Turkish Airlines
Good (4,229 reviews)
Iberia
Good (3,118 reviews)
United Airlines
Good (9,340 reviews)
Air France
Good (1,536 reviews)
Qatar Airways
Good (3,739 reviews)
Emirates
Excellent (3,525 reviews)
Scandinavian Airlines
Good (1,693 reviews)
Air Canada
Good (10,738 reviews)
LOT
Good (1,181 reviews)
Etihad Airways
Good (1,406 reviews)
Finnair
Good (1,365 reviews)
Cathay Pacific
Good (1,176 reviews)
Alaska Airlines
Excellent (11,928 reviews)
TAP AIR PORTUGAL
Good (2,146 reviews)
JetBlue
Good (2,898 reviews)
China Eastern
Good (197 reviews)
Malaysia Airlines
Good (293 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, 949 reviews)
$112+
View
Fairfield Inn & Suites by Marriott Winchester
2 stars
Excellent (8.9, 272 reviews)
$97+
View
La Quinta by Wyndham Winchester
3 stars
Excellent (8.7, 1763 reviews)
$80+
View
Courtyard by Marriott Winchester Medical Center
3 stars
Excellent (8.4, 325 reviews)
$108+
View
Travelodge by Wyndham Winchester
2 stars
Good (7.8, 2064 reviews)
$60+
View
Red Roof Inn Winchester, Va
2 stars
Good (6.3, 757 reviews)
$63+
View

Renting a car in Winchester

Renting a car in Winchester costs $44 per day, on average, or $131 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 19% cheaper than airport locations in Winchester.

Expect to pay $3.26 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 $39.07 and $52.09. 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, 56% cheaper than other rental car types in the city.

Renting a car in Winchester costs $44 per day, on average, or $131 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 19% cheaper than airport locations in Winchester.

Expect to pay $3.26 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 $39.07 and $52.09. 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, 56% cheaper than other rental car types in the city.

Best car rental deals in Winchester

Supplier choice

5 Adults, 5 Bags

$36/day

Supplier choice

Intermediate

5 Adults, 3 Bags

$37/day

Intermediate
Find car rentals in Winchester