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. Winchester deserves at least 2 full days for you to see its main sights.

Where to Eat in Winchester

If you’re looking for affordable options, Village Square Restaurant (103 N Loudoun St) and The American Bar (147 N Loudoun St) are great picks.

When to visit Winchester

Winchester in January
Estimated hotel price
$89
1 night at 3-star hotel
Winchester in January
Estimated hotel price
$89
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 Charlotte and takes around 1h 20m.

Train

Amtrak is the most popular train carrier serving Winchester, followed by Acela. The train journey from Winchester to Baltimore takes 0h 28m 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 Enterprise Rent-A-Car, among others, in Washington, D.C..

Bus

Several bus lines operate bus routes to Winchester, including Peter Pan Bus Lines, Bus and Greyhound. From Philadelphia, the bus ride to Winchester takes 185 miles and will cost you around $44. From New York, the ticket costs about $47 for a journey of 240 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 Charlotte and takes around 1h 20m.

Train

Amtrak is the most popular train carrier serving Winchester, followed by Acela. The train journey from Winchester to Baltimore takes 0h 28m 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 Enterprise Rent-A-Car, among others, in Washington, D.C..

Bus

Several bus lines operate bus routes to Winchester, including Peter Pan Bus Lines, Bus and Greyhound. From Philadelphia, the bus ride to Winchester takes 185 miles and will cost you around $44. From New York, the ticket costs about $47 for a journey of 240 miles.

Airports near Winchester

HGRHagerstown Regional
FDKFrederick

Airlines serving Winchester

KLM
Good (1,364 reviews)
British Airways
Good (7,033 reviews)
Delta
Excellent (7,964 reviews)
Iberia
Good (2,779 reviews)
Air France
Good (1,466 reviews)
United Airlines
Good (8,810 reviews)
Emirates
Excellent (3,273 reviews)
Qatar Airways
Good (3,590 reviews)
Air Canada
Good (9,572 reviews)
Scandinavian Airlines
Good (1,394 reviews)
LOT
Good (1,081 reviews)
Alaska Airlines
Excellent (10,246 reviews)
Finnair
Good (1,292 reviews)
TAP AIR PORTUGAL
Good (1,895 reviews)
Etihad Airways
Good (1,215 reviews)
Singapore Airlines
Excellent (1,310 reviews)
Cathay Pacific
Good (894 reviews)
ITA Airways
Good (994 reviews)
JetBlue
Good (2,925 reviews)
Frontier
Okay (3,300 reviews)
Show more
Find flights to Winchester

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.

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, 878 reviews)
$144+
View
La Quinta Inn & Suites by Wyndham Winchester
3 stars
Excellent (8.8, 1607 reviews)
$102+
View
Holiday Inn Winchester Se-Historic Gateway
3 stars
Excellent (8.7, 814 reviews)
$100+
View
Microtel Inn & Suites by Wyndham Winchester
2 stars
Excellent (8.7, 536 reviews)
$92+
View
Country Inn & Suites by Radisson, Winchester, VA
3 stars
Excellent (8.2, 1922 reviews)
$110+
View
Travelodge by Wyndham Winchester
2 stars
Good (7.8, 1878 reviews)
$70+
View

Renting a car in Winchester

Renting a car in Winchester costs $50 per day, on average, or $100 if you want to rent if for 2 days.

It’s generally cheaper to rent your vehicle outside the airport: locations in the city are around 29% cheaper than airport locations in Winchester.

Expect to pay $3.48 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 $41.79 and $55.72. The most frequently booked car type in Winchester is Full-size (Ford Transit or similar). If you’re looking to save money, though, keep in mind that Compact rental cars (Toyota Prius c or similar) are, on average, 46% cheaper than other rental car types in the city.

Renting a car in Winchester costs $50 per day, on average, or $100 if you want to rent if for 2 days.

It’s generally cheaper to rent your vehicle outside the airport: locations in the city are around 29% cheaper than airport locations in Winchester.

Expect to pay $3.48 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 $41.79 and $55.72. The most frequently booked car type in Winchester is Full-size (Ford Transit or similar). If you’re looking to save money, though, keep in mind that Compact rental cars (Toyota Prius c or similar) are, on average, 46% cheaper than other rental car types in the city.

Best car rental deals in Winchester

Economy

2 Adults, 2 Bags

$46/day

Economy

Supplier choice

5 Adults, 5 Bags

$46/day

Supplier choice
Find car rentals in Winchester

Winchester Travel Guide - View the KAYAK Winchester city guide for the best Winchester travel tips. To help you organize your Winchester trip ideas, this Winchester visitors guide provides travel information and trip tips about how to get there, where to stay, what to do, where to eat and more.