Introduction
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. Consider staying at least one whole day in Winchester to see all of its attractions.

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
C$ 128
1 night at 3-star hotel
Winchester in January
Estimated hotel price
C$ 128
1 night at 3-star hotel

Looking for warm weather? Then head to Winchester in July, when the average temperature is 24 °C, and the highest can go up to 31 °C. The coldest month, on the other hand, is January, when it can get as cold as -5 °C, with an average temperature of 0 °C. You’re likely to see more rain in June, when precipitation is around 100 mm. In contrast, February is usually the driest month of the year in Winchester, with an average rainfall of 56 mm.

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 flight to Winchester from Canada departs from Toronto and takes around 1h 29m.

Train

Amtrak is the only carrier operating train routes to Winchester. The train journey from Winchester to Baltimore takes 0h 32m and costs around C$ 8 for a one-way ticket. When coming by train from Philadelphia, expect to pay about C$ 23 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 102 km from Winchester. You’ll find branches of Budget and Avis, among others, in Washington, D.C..

Bus

Several bus lines operate bus routes to Winchester, including Bus, CoachRun and Peter Pan Bus Lines. From Baltimore, the bus ride to Winchester takes 80 km and will cost you around C$ 30. From Philadelphia, the ticket costs about C$ 56 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 flight to Winchester from Canada departs from Toronto and takes around 1h 29m.

Train

Amtrak is the only carrier operating train routes to Winchester. The train journey from Winchester to Baltimore takes 0h 32m and costs around C$ 8 for a one-way ticket. When coming by train from Philadelphia, expect to pay about C$ 23 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 102 km from Winchester. You’ll find branches of Budget and Avis, among others, in Washington, D.C..

Bus

Several bus lines operate bus routes to Winchester, including Bus, CoachRun and Peter Pan Bus Lines. From Baltimore, the bus ride to Winchester takes 80 km and will cost you around C$ 30. From Philadelphia, the ticket costs about C$ 56 for a journey of 225 km.

Airports near Winchester

HGRHagerstown Regional
FDKFrederick

Airlines serving Winchester

KLM
Good (1,368 reviews)
British Airways
Good (7,093 reviews)
Delta
Excellent (7,964 reviews)
Iberia
Good (2,816 reviews)
Air France
Good (1,467 reviews)
United Airlines
Good (8,846 reviews)
Emirates
Excellent (3,284 reviews)
Qatar Airways
Good (3,589 reviews)
Scandinavian Airlines
Good (1,413 reviews)
Air Canada
Good (9,669 reviews)
LOT
Good (1,092 reviews)
Etihad Airways
Good (1,220 reviews)
Alaska Airlines
Excellent (10,348 reviews)
Finnair
Good (1,311 reviews)
TAP AIR PORTUGAL
Good (1,912 reviews)
Singapore Airlines
Excellent (1,322 reviews)
ITA Airways
Good (999 reviews)
Cathay Pacific
Good (925 reviews)
JetBlue
Good (2,909 reviews)
Malaysia Airlines
Good (265 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 Quality Inn.

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, Excellent reviews)
C$ 190+
View
La Quinta Inn & Suites by Wyndham Winchester
3 stars
Excellent (8.8, Excellent reviews)
C$ 144+
View
Holiday Inn Winchester Se-Historic Gateway
3 stars
Excellent (8.7, Excellent reviews)
C$ 151+
View
Country Inn & Suites by Radisson, Winchester, VA
3 stars
Excellent (8.2, Excellent reviews)
C$ 137+
View
Travelodge by Wyndham Winchester
2 stars
Good (7.8, Good reviews)
C$ 102+
View

Renting a car in Winchester

Expect to pay C$ 1.27 per litre in Winchester (average price from the past 30 days). Depending on the size of your rental car, filling up the tank will cost between C$ 15.18 and C$ 20.24. Compact (Toyota Prius c or similar) is the most popular car type to rent in Winchester, while also 56% cheaper than other types, on average.

Expect to pay C$ 1.27 per litre in Winchester (average price from the past 30 days). Depending on the size of your rental car, filling up the tank will cost between C$ 15.18 and C$ 20.24. Compact (Toyota Prius c or similar) is the most popular car type to rent in Winchester, while also 56% cheaper than other types, on average.

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.