
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.

Motel 6 Southington, CT - Hartford
Price was CA $1,030, price is now CA $929 per person
CA $929
per person
Sep 25 - Oct 1
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to New Haven (HVN)
6.2/10 (1,002 reviews)
The room i was in had an adjacent door to another room. They people in other room were loud and noisy at 1:30am. There should be a way to sound proof door when both rooms are occupied
Reviewed on Jul. 15, 2025

Hilton Garden Inn Hartford North/Bradley Int'l Airport
Price was CA $1,499, price is now CA $1,191 per person
CA $1,191
per person
Sep 25 - Oct 1
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to New Haven (HVN)
8.8/10 Excellent! (1,004 reviews)
It would’ve been better that you had posted that the pool was closed since 2020. My Wife wasn’t too happy about that.
Reviewed on Aug. 18, 2025

Comfort Inn & Suites East Hartford - Hartford
Price was CA $1,394, price is now CA $1,218 per person
CA $1,218
per person
Sep 25 - Oct 1
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to New Haven (HVN)
7.6/10 Good! (1,001 reviews)
Staff friendly and helpful, great breakfast option
Reviewed on Aug. 16, 2025

Residence Inn by Marriott Southington
Price was CA $1,398, price is now CA $1,236 per person
CA $1,236
per person
Sep 25 - Oct 1
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to New Haven (HVN)
8.6/10 Excellent! (557 reviews)
Room was excellent. Easy check in. No sugar with the coffee maker. Traffic is noisy all night long.
Reviewed on Aug. 17, 2025
Cheshire Hotel Deals

Cheshire Welcome Inn
1106 S Main St., Cheshire, CT
The price is CA $136 per night from Aug 24 to Aug 25
CA $136
CA $156 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (716 reviews)
"Comfortable, clean and convenient"
Reviewed on Aug. 7, 2025

The Capitol Hotel
440 Asylum St, Hartford, CT
Fully refundableReserve now, pay when you stay
The price is CA $117 per night from Aug 24 to Aug 25
CA $117
CA $134 total
Aug 24 - Aug 25
includes taxes & fees
7.6/10 Good! (1,018 reviews)
"Good location. Close to train station and downtown. Also across from the train station and across from Bushnell Park"
Reviewed on Aug. 18, 2025

Best Western Executive Hotel Of New Haven - West Haven
490 Saw Mill Rd, West Haven, CT
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from Aug 24 to Aug 25
CA $145
CA $167 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,285 reviews)
"Great location with multiple food options nearby."
Reviewed on Aug. 18, 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.
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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.