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 40m.

Train

Amtrak is the most popular train carrier serving Winchester, followed by Acela. The train journey from Winchester to Baltimore takes 0h 34m and costs around $6 for a one-way ticket. When coming by train from Wilmington, expect to pay about $11 for a 1h 32m 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 Peter Pan Bus Lines, OurBus and Washington Deluxe. From Philadelphia, the bus ride to Winchester takes 177 km and will cost you around $58. From Richmond, the ticket costs about $38 for a journey of 225 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 40m.

Train

Amtrak is the most popular train carrier serving Winchester, followed by Acela. The train journey from Winchester to Baltimore takes 0h 34m and costs around $6 for a one-way ticket. When coming by train from Wilmington, expect to pay about $11 for a 1h 32m 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 Peter Pan Bus Lines, OurBus and Washington Deluxe. From Philadelphia, the bus ride to Winchester takes 177 km and will cost you around $58. From Richmond, the ticket costs about $38 for a journey of 225 km.

Airports near Winchester

HGRHagerstown Regional
FDKFrederick

Airlines serving Winchester

KLM
Good (1,501 reviews)
British Airways
Good (7,896 reviews)
Turkish Airlines
Good (4,317 reviews)
Delta
Good (8,426 reviews)
Iberia
Good (3,185 reviews)
Air France
Good (1,577 reviews)
United Airlines
Good (9,609 reviews)
Scandinavian Airlines
Good (1,750 reviews)
Emirates
Excellent (3,561 reviews)
Qatar Airways
Good (3,730 reviews)
Air Canada
Good (10,943 reviews)
LOT
Good (1,188 reviews)
Finnair
Good (1,390 reviews)
TAP AIR PORTUGAL
Good (2,212 reviews)
Etihad Airways
Good (1,431 reviews)
Cathay Pacific
Good (1,282 reviews)
JetBlue
Good (2,947 reviews)
Alaska Airlines
Good (12,265 reviews)
China Eastern
Good (208 reviews)
Malaysia Airlines
Good (305 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
TownePlace Suites by Marriott Winchester
3 stars
Excellent (9.1, 121 reviews)
$116+
View
Holiday Inn Winchester Se-Historic Gateway By IHG
3 stars
Excellent (8.8, 867 reviews)
$82+
View
Fairfield Inn & Suites by Marriott Winchester
2 stars
Excellent (8.8, 284 reviews)
$101+
View
Courtyard by Marriott Winchester Medical Center
3 stars
Excellent (8.4, 332 reviews)
$113+
View
Country Inn & Suites by Radisson, Winchester, VA
3 stars
Excellent (8.3, 2108 reviews)
$78+
View
Travelodge by Wyndham Winchester
2 stars
Good (7.8, 2103 reviews)
$65+
View

Renting a car in Winchester

Renting a car in Winchester costs $52 per day, on average, or $156 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 13% cheaper than airport locations in Winchester.

Expect to pay $4.47 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 $53.60 and $71.47. 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 $52 per day, on average, or $156 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 13% cheaper than airport locations in Winchester.

Expect to pay $4.47 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 $53.60 and $71.47. 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

Economy

2 Adults, 2 Bags

$40/day

Economy

Supplier choice

5 Adults, 5 Bags

$40/day

Supplier choice
Find car rentals in Winchester