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Hotels in Cheshire

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Choose from 1136 Cheshire Hotel Deals

Holiday Inn Cheshire - Southington by IHG
Holiday Inn Cheshire - Southington by IHG
3 out of 5
64 Knotter Dr, Cheshire, CT
  • 21 min walk from Cheshire Hollow Farm
Stay at this 3-star business-friendly hotel in Cheshire. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.2/10 Very Good! (1,000 reviews)
"Quiet and reasonably priced."

Reviewed on May 22, 2025

Holiday Inn Cheshire - Southington by IHG
Cheshire Welcome Inn
Cheshire Welcome Inn
2.5 out of 5
1106 S Main St., Cheshire, CT
  • 12 min drive from Cheshire Hollow Farm
Stay at this motel in Cheshire. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (677 reviews)
"Quiet, excessive and clean!"

Reviewed on May 24, 2025

Cheshire Welcome Inn
New Haven Hotel
New Haven Hotel
3.5 out of 5
229 George Street, New Haven, CT
  • 41 min drive from Cheshire Hollow Farm
Stay at this 3.5-star business-friendly hotel in New Haven. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,573 reviews)
"Very nice property! So glad we discovered this today! The woman at the front desk was super nice and sweet! Great for a stop over during our trip! The location looks great. Lots of many places nearby. Unfortunately, we probably won’t have time to check them out, hopefully we can find a place for ..."

Reviewed on May 28, 2025

New Haven Hotel
Clarion Inn
Clarion Inn
3 out of 5
201 Washington Avenue, North Haven, CT
  • 26 min drive from Cheshire Hollow Farm
Book a stay at this business-friendly hotel in North Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.4/10 Good! (1,014 reviews)
"Stayed one night as we were passing through!! Clean, quiet, and staff was friendly"

Reviewed on May 21, 2025

Clarion Inn
Holiday Inn Express Southington by IHG
Holiday Inn Express Southington by IHG
2.5 out of 5
120 Laning St, Southington, CT
  • 15 min drive from Cheshire Hollow Farm
Book a stay at this business-friendly hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,004 reviews)
"Property was in a quiet location staff was great but needs some deep cleaning. Stayed in RM 306 bathroom sink cracked,wall had some brown dried pigment by toilet paper, toilet had ring around the bowl, Desk area had dried sticky liquid on it. Bathroom sink counter and floor dusty. Breakfast was ..."

Reviewed on May 25, 2025

Holiday Inn Express Southington by IHG
Omni New Haven Hotel at Yale
Omni New Haven Hotel at Yale
4 out of 5
155 Temple St, New Haven, CT
  • 41 min drive from Cheshire Hollow Farm
Stay at this 4-star business-friendly hotel in New Haven. Enjoy 2 restaurants, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,005 reviews)
"Great spot for graduation. Champagne and ice cream in the lobby was a nice touch."

Reviewed on May 22, 2025

Omni New Haven Hotel at Yale
Hyatt Place Milford / New Haven
Hyatt Place Milford / New Haven
3 out of 5
190 Old Gate Lane, Milford, CT
  • 56 min drive from Cheshire Hollow Farm
Stay at this 3-star business-friendly hotel in Milford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (1,018 reviews)
"Excellent stay and best hotel breakfast in years."

Reviewed on May 20, 2025

Hyatt Place Milford / New Haven
La Quinta Inn & Suites by Wyndham New Haven
La Quinta Inn & Suites by Wyndham New Haven
3 out of 5
400 Sargent Dr, New Haven, CT
  • 42 min drive from Cheshire Hollow Farm
Stay at this 3-star business-friendly hotel in New Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
5.8/10 (1,017 reviews)
"Television did not work."

Reviewed on May 24, 2025

La Quinta Inn & Suites by Wyndham New Haven
Cambria Hotel New Haven University Area
Cambria Hotel New Haven University Area
3 out of 5
20 Dwight Street, New Haven, CT
  • 41 min drive from Cheshire Hollow Farm
Stay at this 3-star business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
8.8/10 Excellent! (745 reviews)
"convenient, 20 minute walk to main yale campus, 30 to science hill"

Reviewed on May 20, 2025

Cambria Hotel New Haven University Area
The Goodwin Hotel
The Goodwin Hotel
3.5 out of 5
1 Haynes St, Hartford, CT
  • 45 min drive from Cheshire Hollow Farm
Stay at this 3.5-star hotel in Hartford. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,003 reviews)
"Hotel was beautiful! The valets were amazing! Would definitely stay there again"

Reviewed on May 22, 2025

The Goodwin Hotel
Courtyard by Marriott Waterbury Downtown
Courtyard by Marriott Waterbury Downtown
3 out of 5
63 Grand St, Waterbury, CT
  • 17 min drive from Cheshire Hollow Farm
Stay at this hotel in Waterbury. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (1,006 reviews)
"The lady at the front desk that checked us in Tuesday night was amazing."

Reviewed on May 24, 2025

Courtyard by Marriott Waterbury Downtown
Hampton Inn & Suites Hartford/East Hartford
Hampton Inn & Suites Hartford/East Hartford
2.5 out of 5
351 Pitkin Steet, East Hartford, CT
  • 46 min drive from Cheshire Hollow Farm
Stay at this hotel in East Hartford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9/10 Wonderful! (1,000 reviews)
"We enjoyed everything from early check in to the indoor pool and breakfast as early as 6am! I just questioned how often the pool is clean it kinda smelled other than that fantastic stay, clean rooms thanks this was East Hartford CT! Me and little one will be going back for sure"

Reviewed on May 27, 2025

Hampton Inn & Suites Hartford/East 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.

Find cheap hotels in Cheshire

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For you, intrepid voyager, Hotwire has a large selection of the best hotels in Cheshire.

Choosing the right hotel in Connecticut has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Cheshire’s 1,136 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $100. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Cheshire hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Cheshire. No matter your reason for visiting Cheshire, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Cheshire hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Cheshire for as low as $100.

How many hotels are there in Cheshire?

With over 1,136 hotels in Cheshire, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $100.

How to find cheap car rentals in Cheshire?

Finding a cheap car rental deal in Cheshire is as easy as scoring cheap hotels in Cheshire. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.