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
New Haven Hotel
229 George Street New Haven CT
Fully refundable
The price is CA $159 per night from Apr 12 to Apr 13
CA $159
CA $183 total
Apr 12 - Apr 13
includes taxes & fees
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundable
The price is CA $151 per night from Apr 12 to Apr 13
CA $151
CA $173 total
Apr 12 - Apr 13
includes taxes & fees
8.6/10 Excellent! (1,258 reviews)
breakfast was fine did not use a/c
Reviewed on Mar 31, 2026
The Capitol Hotel
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
The price is CA $149 per night from Apr 23 to Apr 24
CA $149
CA $172 total
Apr 23 - Apr 24
includes taxes & fees
7.6/10 Good! (1,223 reviews)
It was a short stay but no issues.
Reviewed on Apr 4, 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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- Hotels near Toyota Oakdale Theatre
- B&B in Wallingford
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- Avon Vacations
- Branford Vacations
- Bristol Commons Shopping Center
- Bushnell Park
- Central Connecticut State University
- Coastal Connecticut Vacations
- Connecticut Science Center
- Connecticut State Capital
- Connecticut Vacations
- Derby Vacations
- Elizabeth Park
- Five Mile Point Lighthouse
- Hartford Vacations
- Lighthouse Point Park
- Mark Twain House & Museum
- Milford Plaza Shopping Center
- Monroe Plaza Shopping Center
- Mount Southington Ski Area
- New Britain Vacations
- New Haven Vacations
- Oak Street Beach
- Palace Theatre
- Pilgrim Mall Shopping Center
- Visit Plantsville
- Saint Francis Hospital and Medical Center
- Visit Southington
- Sterling Memorial Library at Yale University
- Unionville Vacations
- 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.
