A stone tower with a metal gate, surrounded by trees and a stone wall.

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Nov 6 - Nov 8
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Our top choices for Cheshire hotels

A landscaped garden with a large rock, yellow flowers, and a weeping willow tree.

1. Cheshire Welcome Inn

Cheshire Welcome Inn
2.5 star property
Cheshire
8.4 out of 10, Very good, (900 reviews)
"Quaint roadside motel"
United States
Jessica
The price is ļæ„12,344
ļæ„14,195 total
includes taxes & fees
Nov 1 - Nov 2
Cheshire Welcome Inn
A Holiday Inn hotel with a covered entrance, multiple floors, and a well-lit facade.

2. Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG
3.0 star property
Southington
8.2 out of 10, Very good, (1,000 reviews)
"Breakfast was delicious and breakfast staff was very nice and very friendly!"
United States
DAVID
The price is ļæ„16,071
ļæ„18,482 total
includes taxes & fees
Nov 29 - Nov 30
Holiday Inn Cheshire - Southington by IHG
A breakfast buffet with various food items, including pastries, bread, and fruits.

3. Quality Inn Waterbury East

Quality Inn Waterbury East
2.5 star property
Waterbury
7.0 out of 10, Good, (1,001 reviews)
"perfect place to stay all clean"
United States
Wilfred
The price is ļæ„13,259
ļæ„15,248 total
includes taxes & fees
Nov 8 - Nov 9
Quality Inn Waterbury East
An outdoor patio area with seating, a fire pit, and umbrellas.

4. Fairfield by Marriott Inn & Suites Wallingford New Haven

Fairfield by Marriott Inn & Suites Wallingford New Haven
3.0 star property
Wallingford
8.6 out of 10, Excellent, (1,003 reviews)
"The hotel was very nice, a comfortable room, nice staff, good breakfast, very convenient location (a minute from the highway) and a reasonable price."
United States
Susie
The price is ļæ„19,711
ļæ„22,668 total
includes taxes & fees
Nov 8 - Nov 9
Fairfield by Marriott Inn & Suites Wallingford New Haven
A hotel lobby with a wooden staircase, a reception desk, and a view through large windows.

5. Econo Lodge Milldale - Southington

Econo Lodge Milldale - Southington
2.0 star property
Milldale
6.6 out of 10, (609 reviews)
"Parking"
United States
LUIS
The price is ļæ„10,044
ļæ„11,551 total
includes taxes & fees
Nov 22 - Nov 23
Econo Lodge Milldale - Southington
A modern bar area with a wooden bar counter, multiple stools, and a variety of liquor bottles.

6. Courtyard New Haven Wallingford

Courtyard New Haven Wallingford
3.0 star property
Wallingford
8.8 out of 10, Excellent, (845 reviews)
"Nice clean property. Pleasant staff"
United States
Tanisha
The price is ļæ„21,964
ļæ„25,258 total
includes taxes & fees
Nov 8 - Nov 9
Courtyard New Haven Wallingford
An outdoor kitchen with a grill and a built-in stove, white chairs, and a red door.

7. Homewood Suites by Hilton Wallingford-Meriden

Homewood Suites by Hilton Wallingford-Meriden
3.0 star property
Wallingford
9.0 out of 10, Wonderful, (1,000 reviews)
"Great stay as always!"
United States
Katja
The price is ļæ„21,294
ļæ„24,488 total
includes taxes & fees
Nov 22 - Nov 23
Homewood Suites by Hilton Wallingford-Meriden
A breakfast buffet area with various food options and a bakery section.

8. Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG
2.5 star property
Southington
8.6 out of 10, Excellent, (1,460 reviews)
"Good breakfast Clean room Perfect for a stay"
Canada
Guillaume
The price is ļæ„15,126
ļæ„17,395 total
includes taxes & fees
Nov 28 - Nov 29
Holiday Inn Express Southington by IHG
An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled floor.

9. Hilton Garden Inn Wallingford/Meriden

Hilton Garden Inn Wallingford/Meriden
3.0 star property
Wallingford
9.0 out of 10, Wonderful, (1,001 reviews)
"Nice stay, clean rooms, comfortable bed"
United States
Jennah
The price is ļæ„20,543
ļæ„23,624 total
includes taxes & fees
Nov 22 - Nov 23
Hilton Garden Inn Wallingford/Meriden
A lobby with a fireplace, seating area, and a reception desk.

10. Comfort Inn & Suites Meriden East

Comfort Inn & Suites Meriden East
2.5 star property
Meriden
7.2 out of 10, Good, (1,001 reviews)
"You can exercise in their gym area, the breakfast is very good, the breakfast lady is very nice, and the reception staff are very attentive."
United States
Nidia
The price is ļæ„12,882
ļæ„14,814 total
includes taxes & fees
Dec 1 - Dec 2
Comfort Inn & Suites Meriden East
A hotel lobby with a modern design, featuring a seating area with sofas, a fireplace, and a television mounted on the wall.

11. Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown
3.0 star property
Waterbury
8.6 out of 10, Excellent, (1,290 reviews)
"Very clean , friendly staff."
United States
gloria
The price is ļæ„14,023
ļæ„16,126 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Waterbury Downtown
An outdoor patio area with a stone fire pit, wicker furniture, and a bar area with a flat-screen TV.

12. Residence Inn by Marriott New Haven Hamden

Residence Inn by Marriott New Haven Hamden
3.0 star property
Hamden
9.4 out of 10, Exceptional, (522 reviews)
"Great nice place with good amenities and breakfast - solid!"
United States
DANIEL
The price is ļæ„22,689
ļæ„26,092 total
includes taxes & fees
Nov 29 - Nov 30
Residence Inn by Marriott New Haven Hamden
A modern lobby with seating, a dining area, and large windows.

13. Clarion Inn North Haven - New Haven North

Clarion Inn North Haven - New Haven North
3.0 star property
North Haven
7.4 out of 10, Good, (1,004 reviews)
"The Clarion is in the middle of a big remodel. New rooms are amazing but common areas are under construction. Amazing staff. Will stay again"
United States
Tina
The price is ļæ„17,062
ļæ„19,621 total
includes taxes & fees
Nov 28 - Nov 29
Clarion Inn North Haven - New Haven North
An outdoor patio area with a fire pit, seating, and a grill.

14. Residence Inn by Marriott Southington

Residence Inn by Marriott Southington
3.0 star property
Southington
8.6 out of 10, Excellent, (678 reviews)
"Everything was good specially breakfast was very good"
United States
Chong
The price is ļæ„22,531
ļæ„25,911 total
includes taxes & fees
Nov 29 - Nov 30
Residence Inn by Marriott Southington
A modern interior with wooden panel walls, a reception desk, and a seating area with chairs.

15. Days Inn by Wyndham Southington

Days Inn by Wyndham Southington
2.0 star property
Southington
7.6 out of 10, Good, (1,001 reviews)
"The staff are extremely nice and professional. The rooms are very clean and comfortable"
United States
Elizabeth
The price is ļæ„13,393
ļæ„15,401 total
includes taxes & fees
Nov 1 - Nov 2
Days Inn by Wyndham Southington
A hotel dining area with a long table, multiple chairs, and a bar counter.

16. Red Roof Inn Meriden

Red Roof Inn Meriden
2.0 star property
Meriden
7.6 out of 10, Good, (1,002 reviews)
"We've stayed here before, and were very happy with our experience. Very quiet, clean, and safe. The staff are great too!!"
United States
Adrienne
The price is ļæ„12,762
ļæ„14,676 total
includes taxes & fees
Nov 1 - Nov 2
Red Roof Inn Meriden
An outdoor patio with a fire pit, wicker furniture, and a pergola structure.

17. Homewood Suites by Hilton Southington, CT

Homewood Suites by Hilton Southington, CT
3.0 star property
Southington
9.2 out of 10, Wonderful, (1,000 reviews)
"Clean room and staff friendliness"
United States
Gopal
The price is ļæ„23,127
ļæ„26,596 total
includes taxes & fees
Nov 8 - Nov 9
Homewood Suites by Hilton Southington, CT
A modern hotel room with a kitchenette, a flat-screen TV mounted on the wall, a desk with a chair, a bed with a blue headboard, and a blue sofa.

18. Holiday Inn Express & Suites Meriden by IHG

Holiday Inn Express & Suites Meriden by IHG
2.5 star property
Meriden
8.4 out of 10, Very good, (1,001 reviews)
"Hotel was clean, well appointed and friendly staff."
United States
John
The price is ļæ„14,968
ļæ„17,213 total
includes taxes & fees
Nov 29 - Nov 30
Holiday Inn Express & Suites Meriden by IHG
A modern hotel with multiple floors, large windows, and a sign for Springhill Suites.

19. Springhill Suites by Marriott Hartford Cromwell

Springhill Suites by Marriott Hartford Cromwell
2.5 star property
Cromwell
8.8 out of 10, Excellent, (795 reviews)
"Enjoyed my stay, Iā€™ll be staying there again."
United States
David
The price is ļæ„25,052
ļæ„28,810 total
includes taxes & fees
Nov 22 - Nov 23
Springhill Suites by Marriott Hartford Cromwell
A Hampton Inn hotel with a modern design, featuring a well-lit entrance and multiple floors.

20. Hampton Inn Waterbury

Hampton Inn Waterbury
2.5 star property
Waterbury
8.0 out of 10, Very good, (1,002 reviews)
"always stay here. great staff, breakfast and room."
United States
John
The price is ļæ„15,401
ļæ„17,711 total
includes taxes & fees
Nov 15 - Nov 16
Hampton Inn Waterbury
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.
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Stay near popular Cheshire attractions

Roaring Brook Park

8.4/10 (12 reviews)
Connecticut's tallest single-drop waterfall cascades dramatically 80 feet through lush woodland. Hike the moderate one-mile loop trail in spring for the most impressive water flow after seasonal rains.
See properties

Learn more about Cheshire

Hikers and nature lovers flock to Cheshire's Farmington Canal Heritage Trail, where paved paths wind through scenic forests and historic landmarks. Families enjoy cooling off at Mixville Recreation Area's swimming pond in summer, while the annual Strawberry Festival offers local treats and community charm.

See all hotels in Cheshire
A stone tower with a metal gate, surrounded by trees and a stone wall.

Top Cheshire Hotel Reviews

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

8/10 Good
"The staff were delightful, great breakfast, and room was clean. Only downside was the outdated shower and horrible shower head/water pressure. Otherwise good stay, would come back again."
Shauna 1-night trip
Posted 18 hours ago
Best Western Executive Hotel Of New Haven - West Haven

More cheap stays in Cheshire

Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

320 E Main St Branford CT
The price is ļæ„10,081 per night from Dec 1 to Dec 2
ļæ„10,081
ļæ„11,751 total
Dec 1 - Dec 2
includes taxes & fees

Frequently asked questions

What's the best place for a stay in Cheshire?
Based on Expedia's traveler preferences, Cheshire Welcome Inn is a top place to stay in Cheshire. Other good choices for your stay in the area are The Capitol Hotel and New Haven Hotel. See all available top hotels, or vacation rentals in Cheshire.
What are some of the best vacation rentals in Cheshire?
New Madison beach house - Ocean front- Great views- booking Summer 2026: This vacation home rental outside of Cheshire is located on the beach and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. See all vacation rentals in Cheshire.
If I need to cancel my hotel reservation in Cheshire, will I receive a refund?
Yes, most hotel room reservations are refundable if you cancel prior to the accommodation's cancellation deadline, which is often 24 or 48 hours before your arrival date. If you have a non-refundable reservation, it might still be possible to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Cheshire.
Where can I learn more about changing or cancelling my trip to Cheshire?
For more information about changing or cancelling your trip to Cheshire, click here.
What is the top LGBTQ-friendly hotel in Cheshire?
Holiday Inn Cheshire - Southington by IHG is a top LGBTQ-friendly hotel, and features free WiFi and sofa beds. See all available hotels listed as LGBTQ-friendly in Cheshire.
Where is the best hotel to stay near Barker Museum?
Holiday Inn Cheshire - Southington, an IHG Hotel is one of the top choices for your stay based on our traveler data, and this 3-star hotel offers a restaurant and an indoor pool. It's located 2.3 mi (3.6 km) from Barker Museum. Other good options within 5 miles include Econo Lodge Milldale - Southington and Cheshire Welcome Inn.
What about the best place to stay near Cheshire Hollow Farm?
One of the top choices for your stay is Holiday Inn Cheshire - Southington, an IHG Hotel, located 1 mi (1.7 km) from Cheshire Hollow Farm, and this 3-star hotel offers a restaurant and an indoor pool. Econo Lodge Milldale - Southington and Homewood Suites by Hilton Southington, CT are two other good options within 5 miles.
What are some accommodations with pools in Cheshire?
Holiday Inn Express Southington by IHG: Features a snack bar/deli, a seasonal outdoor pool, and buffet. Hampton Inn & Suites Hartford/East Hartford and Best Western Executive Hotel Of New Haven - West Haven are a couple of other choices with an onsite pool. View all hotels with pools in Cheshire.
What's the best place to stay near Tweed - New Haven Regional Airport (HVN)?
Quality Inn East Haven - New Haven is a popular hotel, featuring free breakfast and free WiFi. It's located a short 1.3 mi (2.1 km) from Tweed - New Haven Regional Airport. Other good options close to the airport include La Quinta Inn & Suites by Wyndham New Haven and Omni New Haven Hotel at Yale.
How is it to stay in Cheshire?
Visitors to Cheshire are sure to enjoy the restaurants. Tourists can also enjoy the city's waterfalls and shopping. In Cheshire, there are 5 hotels and other accommodations to choose from. Find out more about Cheshire.
What is there to see in Cheshire?
Natural beauty is on display at Drazen Orchards, Bartlem Park, and Roaring Brook Park. A couple of additional sights to add to your agenda are Maplecroft Plaza Shopping Center and Cheshire Hollow Farm. Check out what more to see and do in Expedia's Cheshire guide.
What's the seasonal weather like in Cheshire?
The hottest months are usually July and August with an average temp of 70Ā°F, while the coldest months are January and February with an average of 33Ā°F. Average annual precipitation for Cheshire is 54 inches.

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