Cheshire Vacation Packages
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Your Cheshire Vacation
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 vacation 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 vacation to Cheshire to suit your style of travel, whatever that may look like.
Cheshire Hotel Deals
Cheshire Welcome Inn
1106 S Main St. Cheshire CT
The price is CA $109 per night from Feb 12 to Feb 13
CA $109
CA $125 total
Feb 12 - Feb 13
includes taxes & fees
8.4/10 Very Good! (780 reviews)
Great location, comfortable and clean
Reviewed on Feb 5, 2026
New Haven Hotel
229 George Street New Haven CT
Fully refundable
The price is CA $154 per night from Feb 22 to Feb 23
CA $154
CA $178 total
Feb 22 - Feb 23
includes taxes & fees
9/10 Wonderful! (2,020 reviews)
A+ and great location.
Reviewed on Feb 11, 2026
The Capitol Hotel
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from Feb 12 to Feb 13
CA $120
CA $138 total
Feb 12 - Feb 13
includes taxes & fees
7.6/10 Good! (1,172 reviews)
All good except the sink drain plug got stuck in the drain, no heat in the lobby, and no juice for breakfast. Just coffee, tea, cocoa, and tap water.
Reviewed on Feb 11, 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.
Explore a world of travel with Expedia
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- Avon Vacations
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- Connecticut Science Center
- Connecticut State Capital
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- Saint Francis Hospital and Medical Center
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- Sterling Memorial Library at Yale University
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- Westfield Connecticut Post Mall
- White Memorial Conservation Center
- Yale University Art Gallery
- Yale University
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
