Cheshire Holidays
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Your Cheshire Holiday
There's plenty to love about Cheshire, from its rich history to its spectacular views and beyond. When you're ready to say hello to this lively city, our Cheshire holiday packages will be just the ticket. Any trip to Cheshire needs a well-crafted itinerary. Fill yours with leading attractions like Toyota Oakdale Theatre, Choate Rosemary Hall and Mount Southington Ski Area. Expedia will help you escape your daily routine. Tailor your holiday to Cheshire to suit your style of travel, whatever that may look like.
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 Presents Oakdale Theatre and Powder Ridge Mountain Park and Resort |
Top hotels in Cheshire
Cheshire Welcome Inn
"Sheets and pillow covers had stains on them. The main light in the room flashed like a disco. All the the doors and trim had paint peeling all over the place."
Reviewed on 26 Jun 2026
New Haven Hotel
"Nice location"
Reviewed on 26 Jun 2026
Motel 6 Wethersfield, CT - Hartford
"Stayed at room while volunteering at the Traveler's Golf Tournament. Room had dirty, sticky floor, only one towel, no hangers, toilet seat was filthy and the sink faucet was falling off. Upon checking in a parking pass was given to me to put on the dashboard of my car. Was asked if anyone else was ..."
Reviewed on 26 Jun 2026
Stay near popular Cheshire attractions
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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. Flight-inclusive packages are ATOL protected.
