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.

Where to Eat in Winchester

If you’re looking for affordable options, The American Bar (147 N Loudoun St) and Uno Pizzeria & Grill – Old Town Winchester (103 E Piccadilly St) are great picks.

When to visit Winchester

Winchester in July
Estimated hotel price
C$ 142
1 night at 3-star hotel
Winchester in July
Estimated hotel price
C$ 142
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
Celcius (°C)
Data provided by weatherbase

How to Get to Winchester


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 27m.


Amtrak is the only carrier operating train routes to Winchester. The train journey from Winchester to Baltimore takes 0h 28m and costs around C$ 7 for a one-way ticket. When coming by train from Richmond, expect to pay about C$ 14 for a 1h 50m trip.


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 Thrifty and Dollar, among others, in Washington, D.C..


Several bus lines operate bus routes to Winchester, including Peter Pan Bus Lines, Greyhound and FlixBus. From Baltimore, the bus ride to Winchester takes 56 km and will cost you around C$ 20. From Baltimore, the ticket costs about C$ 41 for a journey of 64 km.

Airports near Winchester

Airlines serving Winchester

Good (504 reviews)
British Airways
Good (2,084 reviews)
Good (3,652 reviews)
Air France
Good (624 reviews)
United Airlines
Good (3,589 reviews)
Good (1,164 reviews)
Qatar Airways
Good (1,684 reviews)
Excellent (1,449 reviews)
Air Canada
Good (2,578 reviews)
Scandinavian Airlines
Good (595 reviews)
Good (783 reviews)
Singapore Airlines
Excellent (582 reviews)
Good (860 reviews)
Good (1,458 reviews)
Alaska Airlines
Good (3,413 reviews)
ITA Airways
Good (304 reviews)
Cathay Pacific
Good (208 reviews)
Malaysia Airlines
Good (104 reviews)
Excellent (282 reviews)
Korean Air
Excellent (447 reviews)
Show more

Where to stay in Winchester

If you’re on a budget, well-reviewed accommodations include Quality Inn and Candlewood Suites Winchester.

Where to stay in popular areas of Winchester

Most booked hotels in Winchester

The George Washington - A Wyndham Grand Hotel
Excellent (8.8, Excellent reviews)
C$ 152+
Holiday Inn Winchester Se-Historic Gateway
Excellent (8.6, Excellent reviews)
C$ 159+
La Quinta Inn & Suites by Wyndham Winchester
Excellent (8.4, Excellent reviews)
C$ 154+
Country Inn & Suites by Radisson, Winchester, VA
Excellent (8.3, Excellent reviews)
C$ 150+
Travelodge by Wyndham Winchester
Good (6.9, Good reviews)
C$ 82+

Renting a car in Winchester

You’re likely to save money by renting your car at the airport: locations in the city are, on average, 35% more expensive than at Washington, D.C. Dulles Intl.

Expect to pay C$ 1.38 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$ 16.50 and C$ 22.00. Economy (Nissan Versa or similar) is the most popular car type to rent in Winchester, while also 5% cheaper than other types, on average.