Search for Cheap Deals on
Hotels in Cheshire

Photo by Tai Bui

Check Last Minute Cheshire Hotel Deals

Tonight Apr 13 - Apr 14Next weekend Apr 18 - Apr 20

Choose from 1131 Cheshire Hotel Deals

Holiday Inn Cheshire - Southington by IHG
Holiday Inn Cheshire - Southington by IHG
3 out of 5
64 Knotter Dr, Cheshire, CT
  • 6 min drive from Barker Character
The price is $116 per night from Apr 20 to Apr 21
$116
includes taxes & fees
Apr 20 - Apr 21
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! (1,004 reviews)
"Excellent"

Reviewed on Apr 6, 2025

Holiday Inn Cheshire - Southington by IHG
Cheshire Welcome Inn
Cheshire Welcome Inn
2.5 out of 5
1106 S Main St., Cheshire, CT
  • 10 min drive from Barker Character
The price is $91 per night from Apr 14 to Apr 15
$91
includes taxes & fees
Apr 14 - Apr 15
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! (661 reviews)
"Very clean and very kind staff. They went above and beyond. Comfortable beds as well"

Reviewed on Apr 6, 2025

Cheshire Welcome Inn
New Haven Hotel
New Haven Hotel
3.5 out of 5
229 George Street, New Haven, CT
  • 38 min drive from Barker Character
The price is $136 per night from Apr 20 to Apr 21
$136
includes taxes & fees
Apr 20 - Apr 21
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! (1,487 reviews)
"Room is big, there are few restaurants near by, within 2-3 min walks. The staff is very friendly and helpful."

Reviewed on Apr 10, 2025

New Haven Hotel
Holiday Inn Express Southington by IHG
Holiday Inn Express Southington by IHG
2.5 out of 5
120 Laning St, Southington, CT
  • 17 min drive from Barker Character
The price is $109 per night from Apr 20 to Apr 21
$109
includes taxes & fees
Apr 20 - Apr 21
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! (1,005 reviews)
"Great"

Reviewed on Apr 9, 2025

Holiday Inn Express Southington by IHG
Cambria Hotel New Haven University Area
Cambria Hotel New Haven University Area
3 out of 5
20 Dwight Street, New Haven, CT
  • 38 min drive from Barker Character
The price is $146 per night from May 4 to May 5
$146
includes taxes & fees
May 4 - May 5
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! (690 reviews)
"Nice and clean."

Reviewed on Apr 8, 2025

Cambria Hotel New Haven University Area
Omni New Haven Hotel at Yale
Omni New Haven Hotel at Yale
4 out of 5
155 Temple St, New Haven, CT
  • 38 min drive from Barker Character
The price is $165 per night from Apr 28 to Apr 29
$165
includes taxes & fees
Apr 28 - Apr 29
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! (1,008 reviews)
"very clean and central"

Reviewed on Apr 11, 2025

Omni New Haven Hotel at Yale
Clarion Inn
Clarion Inn
3 out of 5
201 Washington Avenue, North Haven, CT
  • 23 min drive from Barker Character
The price is $97 per night from Apr 19 to Apr 20
$97
includes taxes & fees
Apr 19 - Apr 20
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! (1,003 reviews)
"Reception was pleasant"

Reviewed on Apr 11, 2025

Clarion Inn
Hyatt Place Milford / New Haven
Hyatt Place Milford / New Haven
3 out of 5
190 Old Gate Lane, Milford, CT
  • 54 min drive from Barker Character
The price is $137 per night from Apr 20 to Apr 21
$137
includes taxes & fees
Apr 20 - Apr 21
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! (1,004 reviews)
"It’s very nice and pleasant here. The rooms are spacious, comfortable and quiet. The fitness room is first rate, the breakfast is great and you get to top off your day by sitting in a nice hot tub in the evening. What more could you ask for?"

Reviewed on Apr 9, 2025

Hyatt Place Milford / New Haven
Courtyard by Marriott Waterbury Downtown
Courtyard by Marriott Waterbury Downtown
3 out of 5
63 Grand St, Waterbury, CT
  • 19 min drive from Barker Character
The price is $91 per night from Apr 20 to Apr 21
$91
includes taxes & fees
Apr 20 - Apr 21
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! (1,002 reviews)
"They had a bar restaurant. You can purchase snacks and it was clean. Beautiful Bobby, and and you could charge your all to your room."

Reviewed on Apr 10, 2025

Courtyard by Marriott Waterbury Downtown
Hyatt House Shelton
Hyatt House Shelton
3 out of 5
830 Bridgeport Ave, Shelton, CT
  • 55 min drive from Barker Character
The price is $128 per night from Apr 20 to Apr 21
$128
includes taxes & fees
Apr 20 - Apr 21
Stay at this 3-star business-friendly hotel in Shelton. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
8.4/10 Very Good! (1,003 reviews)
"Really nice hotel with a good breakfast buffet! Quiet location near many stores and restaurants. Friendly staff"

Reviewed on Apr 9, 2025

Hyatt House Shelton
Hampton Inn by Hilton Shelton
Hampton Inn by Hilton Shelton
2.5 out of 5
695 Bridgeport Ave, Shelton, CT
  • 53 min drive from Barker Character
The price is $136 per night from Apr 28 to Apr 29
$136
includes taxes & fees
Apr 28 - Apr 29
Book a stay at this business-friendly hotel in Shelton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
8.6/10 Excellent! (1,001 reviews)
"."

Reviewed on Apr 9, 2025

Hampton Inn by Hilton Shelton
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
  • 45 min drive from Barker Character
The price is $100 per night from Apr 20 to Apr 21
$100
includes taxes & fees
Apr 20 - Apr 21
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 ...
7.6/10 Good! (1,048 reviews)
"Liked everything"

Reviewed on Apr 9, 2025

Best Western Executive Hotel Of New Haven - West Haven
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

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Cheshire hotel with Hotwire to complete your one-of-a-kind travel checklist.

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 1,131 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 $91. 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 $91.

How many hotels are there in Cheshire?

With over 1,131 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 $91.

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.