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 16 Nov to 17 Nov
AU$141
16 Nov - 17 Nov
includes taxes & fees
8.4/10 Very Good! (751 reviews)
It's a cute little motel near my son's house. We like the convenience and the price. The one negative is when you walk into the room it reeks of cleaning products. It's so strong I was sneezing for the first 15 mins. You get use to it but it never goes away.
Reviewed on 2 Nov 2025
Holiday Inn Express Southington by IHG
120 Laning St, Southington, CT
Fully refundable
The price is AU$146 per night from 16 Nov to 17 Nov
AU$146
16 Nov - 17 Nov
includes taxes & fees
8.6/10 Excellent! (1,148 reviews)
The room was great and the staff was really helpful...
Reviewed on 7 Nov 2025
The Capitol Hotel
440 Asylum St, Hartford, CT
Fully refundableReserve now, pay when you stay
The price is AU$141 per night from 16 Nov to 17 Nov
AU$141
16 Nov - 17 Nov
includes taxes & fees
7.4/10 Good! (1,073 reviews)
Room was good, view was great
Reviewed on 10 Nov 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.
