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
The price is AU$129 per night from 15 Feb to 16 Feb
AU$129
15 Feb - 16 Feb
includes taxes & fees
8.4/10 Very Good! (780 reviews)
Great location, comfortable and clean
Reviewed on 5 Feb 2026
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
The price is AU$204 per night from 22 Feb to 23 Feb
AU$204
22 Feb - 23 Feb
includes taxes & fees
9/10 Wonderful! (2,013 reviews)
A+ and great location.
Reviewed on 11 Feb 2026
The Capitol Hotel
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
The price is AU$143 per night from 16 Feb to 17 Feb
AU$143
16 Feb - 17 Feb
includes taxes & fees
7.6/10 Good! (1,172 reviews)
All good except the sink drain plug got stuck in the drain, no heat in the lobby, and no juice for breakfast. Just coffee, tea, cocoa, and tap water.
Reviewed on 11 Feb 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.
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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.
