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$137 per night from 29 Dec to 30 Dec
AU$137
29 Dec - 30 Dec
includes taxes & fees
8.4/10 Very Good! (770 reviews)
Rooms where clean only thing I didn't like was the parking
Reviewed on 16 Dec 2025
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
The price is AU$200 per night from 29 Dec to 30 Dec
AU$200
29 Dec - 30 Dec
includes taxes & fees
9/10 Wonderful! (1,956 reviews)
Lights in bathroom not bright enough.
Reviewed on 24 Dec 2025
The Capitol Hotel
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
The price is AU$137 per night from 29 Dec to 30 Dec
AU$137
29 Dec - 30 Dec
includes taxes & fees
7.4/10 Good! (1,121 reviews)
Great location and a very clean and comfortable room. The staff was very helpful and went out of their way to help me.
Reviewed on 17 Dec 2025
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.
