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$141 per night from 18 May to 19 May
AU$141
18 May - 19 May
includes taxes & fees
8.4/10 Very Good! (805 reviews)
Only stayed overnight
Reviewed on 11 May 2026
New Haven Hotel
229 George Street New Haven CT
The price is AU$201 per night from 7 June to 8 June
AU$201
7 June - 8 June
includes taxes & fees
9.2/10 Wonderful! (2,120 reviews)
We weren’t happy that parking was $24 a day and that the only part of the breakfast that was free was the coffee. Otherwise, everything else was fine.
Reviewed on 12 May 2026
The Capitol Hotel
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
The price is AU$182 per night from 24 May to 25 May
AU$182
24 May - 25 May
includes taxes & fees
7.4/10 Good! (1,297 reviews)
No breakfast noticed during check out.
Reviewed on 12 May 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.
