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Hotels in Cheshire

Last Minute Hot Rate® Hotel Deals in Cheshire

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Choose from 607 Cheshire Hotel Deals

Courtyard by Marriott Waterbury Downtown
Courtyard by Marriott Waterbury Downtown
3 out of 5
63 Grand St, Waterbury, CT
  • 21 min drive from Cheshire Golf Course
The price is $79 per night from Dec 5 to Dec 5
Located in the heart of Waterbury, this hotel is within a 5-minute walk of Waterbury City Hall, Apothecary Building, and Palace Theatre. Carrie Welton Fountain ...
Courtyard by Marriott Waterbury Downtown
Holiday Inn Cheshire - Southington, an IHG Hotel
Holiday Inn Cheshire - Southington, an IHG Hotel
3 out of 5
64 Knotter Dr, Cheshire, CT
  • 8 min drive from Cheshire Golf Course
The price is $110 per night from Dec 1 to Dec 1
Situated in Cheshire, this hotel is 2.4 mi (3.9 km) from Mount Southington Ski Area and 3 mi (4.8 km) from Barker Museum. Lake Compounce and Quinnipiac University ...
Holiday Inn Cheshire - Southington, an IHG Hotel
Cheshire Welcome Inn
Cheshire Welcome Inn
2.5 out of 5
1106 S Main St., Cheshire, CT
  • 9 min drive from Cheshire Golf Course
The price is $90 per night from Nov 30 to Nov 30
Situated in Cheshire, this motel is 1 mi (1.6 km) from Bartlem Park and within 3 mi (5 km) of Roaring Brook Park and Maplecroft Plaza Shopping Center. Sleeping ...
Cheshire Welcome Inn
New Haven Hotel
New Haven Hotel
3.5 out of 5
229 George Street, New Haven, CT
  • 37 min drive from Cheshire Golf Course
The price is $119 per night from Dec 19 to Dec 19
Located in Downtown New Haven, this hotel is within a 5-minute walk of Shubert Theater and Yale University. New Haven Green and Yale University Art Gallery are ...
New Haven Hotel
Hyatt Place Milford / New Haven
Hyatt Place Milford / New Haven
3 out of 5
190 Old Gate Lane, Milford, CT
  • 53 min drive from Cheshire Golf Course
The price is $97 per night from Dec 20 to Dec 20
Situated in the historical district, this hotel is 0.9 mi (1.4 km) from Westfield Connecticut Post Mall and within 9 mi (15 km) of University of New Haven and ...
Hyatt Place Milford / New Haven
Hilton Garden Inn Milford
Hilton Garden Inn Milford
3 out of 5
291 Old Gate Lane, Milford, CT
  • 52 min drive from Cheshire Golf Course
The price is $101 per night from Dec 19 to Dec 19
Situated in the business district, this hotel is 0.7 mi (1.1 km) from Westfield Connecticut Post Mall and within 3 mi (5 km) of Robert Treat Farm and Gulf Beach. ...
Hilton Garden Inn Milford
The Goodwin Hotel
The Goodwin Hotel
3.5 out of 5
1 Haynes St, Hartford, CT
  • 47 min drive from Cheshire Golf Course
The price is $169 per night from Dec 22 to Dec 22
Located in Downtown Hartford, this hotel is within a 5-minute walk of Theater Works and XL Center. Connecticut Convention Center and Hartford Hospital are also ...
The Goodwin Hotel
Holiday Inn Express Hartford South - Rocky Hill, an IHG Hotel
Holiday Inn Express Hartford South - Rocky Hill, an IHG Hotel
2.5 out of 5
20 Waterchase Drive, Rocky Hill, CT
  • 38 min drive from Cheshire Golf Course
The price is $108 per night from Dec 13 to Dec 13
Situated in Rocky Hill, this golf hotel is within 9 mi (15 km) of Connecticut Convention Center, Connecticut Science Center, and Bushnell Park. XL Center and ...
Holiday Inn Express Hartford South - Rocky Hill, an IHG Hotel
HYATT house Shelton
HYATT house Shelton
3 out of 5
830 Bridgeport Ave, Shelton, CT
  • 55 min drive from Cheshire Golf Course
The price is $118 per night from Dec 19 to Dec 19
Situated in the entertainment district, this hotel is 0.4 mi (0.7 km) from Roosevelt Forest and 2.7 mi (4.3 km) from Bishop Wicke Health Center. SportsCenter ...
HYATT house Shelton
The Blake Hotel
The Blake Hotel
4 out of 5
9 High Street, New Haven, CT
  • 37 min drive from Cheshire Golf Course
The price is $199 per night from Dec 12 to Dec 12
Located in Downtown New Haven, this hotel is within a 10-minute walk of Yale University Art Gallery, Yale University, and Yale-New Haven Hospital. University ...
The Blake Hotel
The Capitol Hotel, Ascend Hotel Collection
The Capitol Hotel, Ascend Hotel Collection
3 out of 5
440 Asylum St, Hartford, CT
  • 47 min drive from Cheshire Golf Course
The price is $88 per night from Dec 12 to Dec 12
Located in Downtown Hartford, this hotel is within 1 mi (2 km) of Theater Works, XL Center, and Connecticut Convention Center. Hartford Hospital and Mark Twain ...
The Capitol Hotel, Ascend Hotel Collection
Hilton Hartford
Hilton Hartford
3.5 out of 5
315 Trumbull St, Hartford, CT
  • 48 min drive from Cheshire Golf Course
The price is $131 per night from Dec 24 to Dec 24
Located in Downtown Hartford, this hotel is within a 5-minute walk of Hartford Stage and XL Center. Connecticut Convention Center and Xfinity Theatre are also ...
Hilton Hartford
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.

HOTW-Hotel-Deals-726-959@2x.jpg (1918×258)*Savings based on Hot Rate® hotel bookings as compared with the lowest published rates found on leading retail travel sites. Hot Rates are different from retail rates. With Hot Rates you enter the date, location and star rating. Hotel revealed only after booking. All bookings final.

Cheshire is calling — find the perfect hotel

Everyone wants to score a deal on travel, but price is just one factor to consider when booking an unforgettable hotel. Whether you’re visiting family, attending a conference or taking a well-earned vacation in Cheshire, having an awesome experience should be a no-brainer.

Hotwire will hook you up! From restful nights near your flight to that prime spot in the city’s heart, we’ve done our research to bring the best options to your fingertips. Book your Cheshire hotel with us now and start your next adventure.

You’re not the average traveler — and we know it

You’ve done your homework and know exactly where you want to go. We’re here to help with some Hotwire travel geek-approved tips on how to save on your booking.

Get away for the weekend

Hotels in bigger cities usually charge higher rates during the week, when people are traveling for business. Weekends can be a bargain! It’s the other way around for vacation spots, so if you’re looking for a beach escape, consider a mid-week trip.

Give yourself some wiggle room

If your plans are flexible, play around with some different travel dates – a shift of a few days either way can help you save big. Prices usually jump the weekends before and after popular holidays, so we recommend steering clear of them. Or consider visiting during the off-season, when prices are generally lower.

Plan around big events

Are prices surprisingly high? There might be a huge conference or festival in town. Consider shifting your dates if you can. Of course, if that’s why you’re going, you’ll have to bite the bullet. We’ll still work to get you the best rates out there.

Noodle over new adventures

Set aside time to plan what you want to see, taste and discover. Nothing completes a trip, big or small, like a few new experiences! Check city apps or area websites to find out what’s new and what events are happening during your stay. Even during a family reunion, you can detour to that locals-only fish taco stand or under-the-radar music club. Your cousins will be impressed.

Frequently Asked Questions About Cheshire

When is the best time of the year to find Cheshire hotel deals?

is the best time to find cheap Cheshire hotel deals.

When should I vacation to Cheshire?

are very popular times to take vacations to Cheshire.

Where can I find the best last minute travel deals for Cheshire?

Only on Hotwire can you find last minute hotel deals for over 607 Cheshire hotels. Save big with Hot Rate - score exclusive, unbeatable deals from our hotel suppliers.

What if I have to cancel my trip to Cheshire?

The fastest path to canceling your booking is through one of our self-serve tools found at https://vacation.hotwire.com/lp/coronavirus-travel

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