Cheshire Holidays
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Your Cheshire Holiday
Book a Cheshire holiday package and get set for a fabulous getaway. With a reputation for its rich history and spectacular views, there's plenty to keep you on the go in this fascinating city. Every trip to Cheshire needs a well-crafted itinerary. Fill yours with famous sights like Toyota Oakdale Theatre, Choate Rosemary Hall and Sleeping Giant State Park. Whatever your travel plans or the size of your budget, putting together a tailored Cheshire holiday is easy with Expedia.
Cheshire Holiday
Cheshire Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Tweed - New Haven Regional Airport (HVN) |
Population | 29,400 |
Max Temp Winter | 2ºC |
Max Temp Summer | 27ºC |
Top Sights | Lake Compounce, Toyota Oakdale Theatre and Powder Ridge Mountain Park and Resort |
Our pick of the best Cheshire Hotel Deals
Cheshire Welcome Inn
1106 S Main St. Cheshire CT
Fully refundableReserve now, pay when you stay
The price is AU$149 per night from 1 July to 2 July
AU$149
1 July - 2 July
includes taxes & fees
8.4/10 Very good! (832 reviews)
"Sheets and pillow covers had stains on them. The main light in the room flashed like a disco. All the the doors and trim had paint peeling all over the place."
Reviewed on 26 June 2026
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
The price is AU$197 per night from 26 July to 27 July
AU$197
26 July - 27 July
includes taxes & fees
9.2/10 Wonderful! (2,200 reviews)
"The room was clean, the staff were friendly, and parking was easy and safe."
Reviewed on 27 June 2026
Motel 6 Wethersfield, CT - Hartford
1341 Silas Deane Hwy Wethersfield CT
Fully refundableReserve now, pay when you stay
The price is AU$123 per night from 1 July to 2 July
AU$123
1 July - 2 July
includes taxes & fees
7/10 Good! (1,197 reviews)
"Stayed at room while volunteering at the Traveler's Golf Tournament. Room had dirty, sticky floor, only one towel, no hangers, toilet seat was filthy and the sink faucet was falling off. Upon checking in a parking pass was given to me to put on the dashboard of my car. Was asked if anyone else was ..."
Reviewed on 26 June 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Cheshire attractions
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
