Cheshire Vacation Packages

Right now's the time to craft your dream Cheshire vacation. Sit back and let the brilliant staff at Orbitz bundle up amazing hotel and flight deals for you. You'll be able to save up to when you bundle up! All you have to do is select your preferred hotels, airfares, rental cars and experiences. And that's not all — you can customize your travels by selecting from 500 airline partners and no less than 500,000 accommodations across the globe. You have the flexibility! There are unlimited options to tailor your own extraordinary vacation, whatever your style, budget or needs.

Where is Cheshire?

Cheshire — you've heard so much about it, you're hankering to go there but don't have a clue where it is? Allow us to point you in the right direction. Cheshire lies 5 miles north of Adams. You'll also find it 9 miles southwest of Pittsfield. The population of this area of The Berkshires is roughly 500.

Car Rentals in Cheshire

Explore the region on your own terms by checking out car rentals in Cheshire through Orbitz. Start your engines and tighten your seatbelt — it's time to step on the gas!

Where to stay in Cheshire – Hotel Accommodation

You'd better not hesitate too long! There are only 3 hotels in Cheshire. Book with Orbitz right now so you don't miss out. The Spring's Inn and The Weathervane Motel are great accommodation choices here.

Nearest Airports to Cheshire

Spur-of-the-moment getaways can be thrilling, but it's still a good idea to know a little about where you're going. The nearest airport to Cheshire is Bradley International Airport (BDL), 50 miles southeast of the downtown area.

Popular Places to Visit Near Cheshire

Go to Cheshire for its unmistakeable character and style. Though, you also have esteemed tourist attractions right under your nose! Tourists from near and far head to the Egg. You can access it easily from Delmar, 35 miles away.

No Cancellation Fees

Need to cancel or amend your booking? Worried about getting hit with a fee? You'll be delighted to hear that we don't have one!^ Fingers crossed, your hotel and airline don't either, but it's a wise idea to get in touch with them beforehand to find out.