Introduction
Where to eat
When to visit
How to get there
Where to stay
Renting a car

Cheshire travel guide

Cheshire Tourism | Cheshire Guide

You're Going to Love Cheshire

With a population of 29,443, Cheshire is a must-see destination in Connecticut, United States. It is among the most popular tourist destinations in the country. Cheshire deserves at least 2 full days for you to see its main sights.

Where to Eat in Cheshire

If you’re looking for affordable options, Viron Rondo Osteria (1721 Highland Ave) and Il Gusto Italian Wine and Bar (286 Maple Ave) are great picks.

When to visit Cheshire

Cheshire in February
Estimated hotel price
$96
1 night at 3-star hotel
Cheshire in February
Estimated hotel price
$96
1 night at 3-star hotel

How to Get to Cheshire

Plane

Although Cheshire doesn’t have its own airport, you can fly to Islip Long Island (ISP), which is located 51 miles from Cheshire. New York LaGuardia Airport is the most popular, with regular flights from American Airlines, Aeromexico, Delta and other airlines departing from the United States. The shortest domestic flight to Cheshire departs from Raleigh and takes around 1h 34m.

Train

Amtrak is the only carrier operating train routes to Cheshire. The train journey from Cheshire to Washington, D.C. takes 0h 02m and costs around $101 for a one-way ticket. When coming by train from New York, expect to pay about $11 for a 1h 50m trip.

Car

Another option to get to Cheshire is to pick up a car rental from New York, which is about 76 miles from Cheshire. You’ll find branches of Turo and Payless, among others, in New York.

Plane

Although Cheshire doesn’t have its own airport, you can fly to Islip Long Island (ISP), which is located 51 miles from Cheshire. New York LaGuardia Airport is the most popular, with regular flights from American Airlines, Aeromexico, Delta and other airlines departing from the United States. The shortest domestic flight to Cheshire departs from Raleigh and takes around 1h 34m.

Train

Amtrak is the only carrier operating train routes to Cheshire. The train journey from Cheshire to Washington, D.C. takes 0h 02m and costs around $101 for a one-way ticket. When coming by train from New York, expect to pay about $11 for a 1h 50m trip.

Car

Another option to get to Cheshire is to pick up a car rental from New York, which is about 76 miles from Cheshire. You’ll find branches of Turo and Payless, among others, in New York.

Airports near Cheshire

LGANew York LaGuardia
HPNWhite Plains Westchester County
ISPIslip Long Island

Airlines serving Cheshire

Lufthansa
Good (7,044 reviews)
KLM
Good (1,334 reviews)
British Airways
Good (6,836 reviews)
SWISS
Good (1,588 reviews)
Delta
Excellent (7,935 reviews)
Turkish Airlines
Good (3,790 reviews)
Iberia
Good (2,698 reviews)
Air France
Good (1,446 reviews)
Austrian Airlines
Good (780 reviews)
United Airlines
Good (8,696 reviews)
Emirates
Excellent (3,215 reviews)
Qatar Airways
Good (3,563 reviews)
Air Canada
Good (9,243 reviews)
Scandinavian Airlines
Good (1,349 reviews)
Brussels Airlines
Good (346 reviews)
LOT
Good (1,069 reviews)
Finnair
Good (1,275 reviews)
Alaska Airlines
Excellent (9,967 reviews)
TAP AIR PORTUGAL
Good (1,851 reviews)
Etihad Airways
Good (1,203 reviews)
Show more

Where to stay in popular areas of Cheshire

Most booked hotels in Cheshire

See all
Homewood Suites by Hilton Southington, CT
3 stars
Excellent (8.6, 325 reviews)
$168+
View
Hilton Garden Inn Wallingford/Meriden
3 stars
Excellent (8.5, 504 reviews)
$173+
View
Holiday Inn Express Southington
2 stars
Excellent (8.4, 428 reviews)
$128+
View
Cheshire Welcome Inn
2 stars
Excellent (8.2, 390 reviews)
$81+
View
Holiday Inn Cheshire - Southington
3 stars
Good (7.8, 440 reviews)
$123+
View
Comfort Inn & Suites
2 stars
Good (7.2, 814 reviews)
$96+
View

Renting a car in Cheshire

Renting a car in Cheshire costs $60 per day, on average, or $119 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 30% cheaper than airport locations in Cheshire.

Expect to pay $3.41 per gallon in Cheshire (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 Cheshire is Full-size (Chevrolet Suburban or similar). If you’re looking to save money, though, keep in mind that Supplier choice rental cars (Class Special Car or similar) are, on average, 60% cheaper than other rental car types in the city.

Renting a car in Cheshire costs $60 per day, on average, or $119 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 30% cheaper than airport locations in Cheshire.

Expect to pay $3.41 per gallon in Cheshire (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 Cheshire is Full-size (Chevrolet Suburban or similar). If you’re looking to save money, though, keep in mind that Supplier choice rental cars (Class Special Car or similar) are, on average, 60% cheaper than other rental car types in the city.

Find car rentals in Cheshire

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