Cheshire Vacations
Book a Hotel + Flight or Car together to unlock savings
Photo by Tai Bui
- Plan, book, travel with confidence
Better together
Save up to ￥45,448 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Find the Best Cheshire Vacation Packages
Cheshire Hotel Deals
Cheshire Welcome Inn
1106 S Main St., Cheshire, CT
The price is ￥14,514 per night from Sep 24 to Sep 25
￥14,514
￥16,691 total
Sep 24 - Sep 25
includes taxes & fees
8.4/10 Very Good! (728 reviews)
"It is always a pleasure to stay here. We return to the area (from Florida) once a year to visit w/family and friends. The hotel property is very clean, thoughtful layout of our room and amenities it offers: microwave and fridge; large mirror; ample clothes rack; desk/chair. I really like the long ..."
Reviewed on Sep 12, 2025
The Capitol Hotel
440 Asylum St, Hartford, CT
Fully refundableReserve now, pay when you stay
The price is ￥13,662 per night from Sep 23 to Sep 24
￥13,662
￥15,711 total
Sep 23 - Sep 24
includes taxes & fees
7.4/10 Good! (1,048 reviews)
"Property was very clean, staff were very nice and helpful the bed was very comfortable and the room was well appointed."
Reviewed on Sep 19, 2025
Best Western Hartford Hotel & Suites
185 Brainard Rd, Hartford, CT
Fully refundableReserve now, pay when you stay
The price is ￥13,999 per night from Sep 28 to Sep 29
￥13,999
￥16,099 total
Sep 28 - Sep 29
includes taxes & fees
7.6/10 Good! (1,006 reviews)
"Excellent hotel. Close to everything. Friendly staff"
Reviewed on Sep 9, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
