Introduction
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 18,368, Winchester is a must-see destination in Kentucky, 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.

When to visit Winchester

Winchester in January
Estimated hotel price
$82
1 night at 3-star hotel
Winchester in January
Estimated hotel price
$82
1 night at 3-star hotel

How to Get to Winchester

Plane

Although Winchester doesn’t have its own airport, you can fly to Lexington Blue Grass (LEX), which is located 23 miles from Winchester. Louisville Airport is the most popular, with regular flights from American Airlines, Delta, WestJet and other airlines departing from the United States. The shortest domestic flight to Winchester departs from Fort Lauderdale and takes around 2h 23m.

Car

Another option to get to Winchester is to pick up a car rental from Nashville, which is about 191 miles from Winchester. You’ll find branches of Turo and NU Car, among others, in Nashville.

Bus

Several bus lines operate bus routes to Winchester, including Greyhound, FlixBus and Tornado Bus. From Nashville, the bus ride to Winchester takes 70 miles and will cost you around $90. From Chicago, the ticket costs about $112 for a journey of 510 miles.

Plane

Although Winchester doesn’t have its own airport, you can fly to Lexington Blue Grass (LEX), which is located 23 miles from Winchester. Louisville Airport is the most popular, with regular flights from American Airlines, Delta, WestJet and other airlines departing from the United States. The shortest domestic flight to Winchester departs from Fort Lauderdale and takes around 2h 23m.

Car

Another option to get to Winchester is to pick up a car rental from Nashville, which is about 191 miles from Winchester. You’ll find branches of Turo and NU Car, among others, in Nashville.

Bus

Several bus lines operate bus routes to Winchester, including Greyhound, FlixBus and Tornado Bus. From Nashville, the bus ride to Winchester takes 70 miles and will cost you around $90. From Chicago, the ticket costs about $112 for a journey of 510 miles.

Airports near Winchester

SDFLouisville Intl
CVGCincinnati Cinci./N. Kentucky
LEXLexington Blue Grass

Airlines serving Winchester

Lufthansa
Good (7,044 reviews)
KLM
Good (1,334 reviews)
British Airways
Good (6,837 reviews)
SWISS
Good (1,588 reviews)
Delta
Excellent (7,934 reviews)
Turkish Airlines
Good (3,790 reviews)
Iberia
Good (2,698 reviews)
Air France
Good (1,446 reviews)
United Airlines
Good (8,696 reviews)
Emirates
Excellent (3,215 reviews)
Qatar Airways
Good (3,563 reviews)
Air Canada
Good (9,245 reviews)
Scandinavian Airlines
Good (1,349 reviews)
Brussels Airlines
Good (346 reviews)
Finnair
Good (1,275 reviews)
Alaska Airlines
Excellent (9,968 reviews)
ITA Airways
Good (967 reviews)
Aer Lingus
Good (1,076 reviews)
Malaysia Airlines
Good (254 reviews)
Spirit Airlines
Good (7,962 reviews)
Show more
Find flights to Winchester

Where to stay in Winchester

If you’re on a budget, well-reviewed accommodations include Baymont by Wyndham Winchester and Best Western Winchester Hotel.

Where to stay in popular areas of Winchester

Most booked hotels in Winchester

See all
Holiday Inn Express Lexington East - Winchester
2 stars
Excellent (8.9, 245 reviews)
$117+
View
Holiday Inn Express & Suites Mt Sterling North
2 stars
Excellent (8.4, 198 reviews)
$145+
View
Hampton Inn Winchester
2 stars
Excellent (8, 165 reviews)
$155+
View
Best Western Winchester Hotel
2 stars
Good (7.7, 432 reviews)
$99+
View
Comfort Inn & Suites
2 stars
Good (7.4, 347 reviews)
$94+
View
Baymont by Wyndham Winchester
2 stars
Good (6.8, 301 reviews)
$76+
View

Renting a car in Winchester

Renting a car in Winchester costs $73 per day, on average, or $147 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 2% cheaper than airport locations in Winchester.

Expect to pay $3.41 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 $40.88 and $54.51. The most frequently booked car type in Winchester is Compact (Nissan Rogue or similar). If you’re looking to save money, though, keep in mind that Premium rental cars (RAM Pickup or similar) are, on average, 10% cheaper than other rental car types in the city.

Renting a car in Winchester costs $73 per day, on average, or $147 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 2% cheaper than airport locations in Winchester.

Expect to pay $3.41 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 $40.88 and $54.51. The most frequently booked car type in Winchester is Compact (Nissan Rogue or similar). If you’re looking to save money, though, keep in mind that Premium rental cars (RAM Pickup or similar) are, on average, 10% cheaper than other rental car types in the city.

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.