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.
Top Cheshire Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Red Roof Inn Milford - New Haven
Price was CA $1,217, price is now CA $1,172 per person
CA $1,172
per person
Jun 27 - Jul 1
found 2 hours ago
Roundtrip flight included
Winnipeg (YWG) to New Haven (HVN)
7/10 Good! (1,003 reviews)
The ice machine wasn't working. Neither one. Bur the staff was so nice!! It was clean and close to everything.. I will definitely stay there again.
Reviewed on Apr 12, 2026
Springhill Suites Milford
Price was CA $1,567, price is now CA $1,527 per person
CA $1,527
per person
Jun 27 - Jul 1
found 2 hours ago
Roundtrip flight included
Winnipeg (YWG) to New Haven (HVN)
8.6/10 Excellent! (1,000 reviews)
Clean modern room. Spacious bathroom. Staff very friendly. Nice selection for breakfast.
Reviewed on Apr 8, 2026
Cheshire Hotel Deals
New Haven Hotel
229 George Street New Haven CT
Fully refundable
The price is CA $168 per night from May 3 to May 4
CA $168
CA $194 total
May 3 - May 4
includes taxes & fees
9.2/10 Wonderful! (2,086 reviews)
Hotel is in a great location, perfect for walking around the area. Nearby parking is very convenient, but tight. Staff was friendlt, everything was clean, room was large and quality was fantastic. Would stay here again.
Reviewed on Apr 12, 2026
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundable
The price is CA $149 per night from Apr 19 to Apr 20
CA $149
CA $172 total
Apr 19 - Apr 20
includes taxes & fees
8.6/10 Excellent! (1,269 reviews)
Room was clean. Breakfast was good
Reviewed on Apr 12, 2026
The Capitol Hotel
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from Apr 26 to Apr 27
CA $119
CA $137 total
Apr 26 - Apr 27
includes taxes & fees
7.6/10 Good! (1,236 reviews)
Safe parking family friendly very clean environment close the train station i love it there.
Reviewed on Apr 12, 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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- Bristol Commons Shopping Center
- Bushnell Park
- Central Connecticut State University
- Coastal Connecticut Vacations
- Connecticut Science Center
- Connecticut State Capital
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- Elizabeth Park
- Five Mile Point Lighthouse
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- Mark Twain House & Museum
- Milford Plaza Shopping Center
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- Mount Southington Ski Area
- New Britain Vacations
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- 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
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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.
