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Choose from 1223 Cheshire Hotel Deals

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
  • 41 min drive from Cheshire Hollow Farm
Book a stay at this business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
9/10 Wonderful! (2,004 reviews)
Staff was awesome.

Reviewed on Jan 19, 2026

New Haven Hotel
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
  • 45 min drive from Cheshire Hollow Farm
Book a stay at this business-friendly hotel in Hartford. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
7.4/10 Good! (1,153 reviews)
Friendly staff, easy and typical buffet breakfast. Walking distance to all major downtown Hartford attractions. Will use again if needed.

Reviewed on Jan 19, 2026

The Capitol Hotel
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St Branford CT
  • 46 min drive from Cheshire Hollow Farm
Stay at this motel in Branford. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7/10 Good! (1,004 reviews)
Everything was beautiful

Reviewed on Jan 18, 2026

Motel 6 New Haven - Branford, CT
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
Book a stay at this business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,003 reviews)
Friendly & helpful staff & bartenders

Reviewed on Jan 16, 2026

Cambria Hotel New Haven University Area
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! (1,208 reviews)
There was little water pressure in the bathroom shower. The rooms need a deep clean, food stain on the walls. Beds were very comfortable and it was quiet.

Reviewed on Jan 20, 2026

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
Book a stay at this business-friendly hotel in New Haven. Enjoy 2 restaurants, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,006 reviews)
Nice Room - Overlooks Yale’s campus.

Reviewed on Jan 19, 2026

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
Book a stay at this business-friendly hotel in Milford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.4/10 Very Good! (1,227 reviews)
All is good

Reviewed on Jan 17, 2026

Hyatt Place Milford / New Haven
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. ...
8.8/10 Excellent! (1,107 reviews)
Dana the front desk associate was sooo nice and helpful!

Reviewed on Jan 21, 2026

Hampton Inn & Suites Hartford/East Hartford
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. ...
8.2/10 Very Good! (1,111 reviews)
Didnt know about the breakfast. Staff was great

Reviewed on Jan 19, 2026

Courtyard by Marriott Waterbury Downtown
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
490 Saw Mill Rd West Haven CT
  • 47 min drive from Cheshire Hollow Farm
Book a stay at this business-friendly hotel in West Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,532 reviews)
Parking is good. Breakfast must consist a vegetable and salads.

Reviewed on Jan 20, 2026

Best Western Executive Hotel Of New Haven - West Haven
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

2.5 out of 5
1 Batterson Park Rd Farmington CT
  • 29 min drive from Cheshire Hollow Farm
Book a stay at this business-friendly hotel in Farmington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7.8/10 Good! (1,002 reviews)
Room was not "dirty" but also not thoroughly cleaned. Towels were stained and had hair. Staff was very friendly. Parking lot could use more lighting.

Reviewed on Jan 13, 2026

Extended Stay America Suites Hartford Farmington
Comfort Inn Wethersfield - Hartford

Comfort Inn Wethersfield - Hartford

2.5 out of 5
1330 Silas Deane Hwy Wethersfield CT
  • 37 min drive from Cheshire Hollow Farm
Book a stay at this business-friendly hotel in Wethersfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
5.4/10 (1,000 reviews)
Had great stay and good nights sleep. I am almost certain that I will return again.

Reviewed on Jan 1, 2026

Comfort Inn Wethersfield - 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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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 1,223 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 $78. 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.

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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 $78.

How many hotels are there in Cheshire?

With over 1,223 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 $78.

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.