Cheshire Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Tai Bui
- Plan, book, travel with confidence
Better together
Save up to AU$703 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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$173 per night from 28 Sept to 29 Sept
AU$173
28 Sept - 29 Sept
includes taxes & fees
8.4/10 Very Good! (732 reviews)
"It was a good room nothing fancy but a good 4 star Clean quiet and good parking"
Reviewed on 22 Sept 2025
The Capitol Hotel
440 Asylum St, Hartford, CT
Fully refundableReserve now, pay when you stay
The price is AU$161 per night from 1 Oct to 2 Oct
AU$161
1 Oct - 2 Oct
includes taxes & fees
7.4/10 Good! (1,072 reviews)
"Very nice and spacious room, clean and well maintained"
Reviewed on 24 Sept 2025
Best Western Hartford Hotel & Suites
185 Brainard Rd, Hartford, CT
Fully refundableReserve now, pay when you stay
The price is AU$184 per night from 5 Oct to 6 Oct
AU$184
5 Oct - 6 Oct
includes taxes & fees
7.6/10 Good! (1,002 reviews)
"The personal was very nice, Stephanie was exceptional"
Reviewed on 24 Sept 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
