Cheshire, CT

Travel Guide

A stone tower with a metal gate, surrounded by trees and a stone wall.
A frozen lake with a solitary tree in the foreground and a sunset in the background.
A wooden bridge over a river with a forested area in the background.
A stone tower with American flags in front.
A road flanked by autumn trees with sunlight filtering through.
Cheshire Welcome Inn

Cheshire Welcome Inn

2.5 out of 5
1106 S Main St. Cheshire CT
$99 nightly
The price is $114 total per night from Jul 6 to Jul 7
$114 total
Jul 6 - Jul 7
Total with taxes and fees
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! (834 reviews)
"The room was clean. There was ample parking. And most of all, for us the location was convenient. However, this motel is showing its age. The air conditioning in unreliable, and the rooms are small."

Reviewed on Jun 29, 2026

Cheshire Welcome Inn
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
$106 nightly
The price is $121 total per night from Jul 6 to Jul 7
$121 total
Jul 6 - Jul 7
Total with taxes and fees
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 ...
9.2/10 Wonderful! (2,193 reviews)
"If you're looking for a downtown hotel for a night or two, this is a great location. Parking is available in the ramp across the street. Easy peasy. Lobby is large, rooms are clean. My only suggestion is the front desk staff needs to be a bit more informed about the area.... what's open later at ..."

Reviewed on Jul 2, 2026

New Haven Hotel
Hilton Garden Inn Milford

Hilton Garden Inn Milford

3 out of 5
291 Old Gate Lane Milford CT
$113 nightly
The price is $130 total per night from Aug 2 to Aug 3
$130 total
Aug 2 - Aug 3
Total with taxes and fees
Stay at this hotel in Milford. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.6/10 Excellent! (1,005 reviews)
"Design, staff, roomy and clean"

Reviewed on Jul 2, 2026

Hilton Garden Inn Milford
See all 1,282 properties in Cheshire
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.
Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
240 Congress Avenue New Haven CT
Stay at this aparthotel in New Haven. Enjoy free WiFi, free parking, and a rooftop terrace. Popular attractions Shubert Theater and Knights of Columbus Museum ...
9.6/10 Exceptional! (84 reviews)
"Amazing rental. It was perfect!"

Reviewed on Jun 20, 2026

Luxury Furnished Apartments by Hyatus Downtown at Yale
TREETOPS! A Reunion/Retreat/Event estate! JULY OPENINGS Seasonal POOL! Sleeps 12

TREETOPS! A Reunion/Retreat/Event estate! JULY OPENINGS Seasonal POOL! Sleeps 12

Guilford CT
Stay at this vacation home in Guilford. Enjoy free WiFi, private pools, and a garden. Popular attractions Chaffinch Island State Park and Guilford Town Green ...
10/10 Exceptional! (46 reviews)
"We had an amazing weekend! The house was sparkling clean, and Dan was super helpful. Treetops is a gorgeous, fascinating house. We really enjoyed the pool, the sound system, and the deck. Great birdwatching!! The house is very quiet and feels remote, but was minutes from town and beaches. We hope ..."

Reviewed on Jun 21, 2026

TREETOPS! A Reunion/Retreat/Event estate! JULY OPENINGS Seasonal POOL! Sleeps 12
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
9 Tower Ln New Haven CT
Book a stay at this business-friendly aparthotel in New Haven. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Knights of Columbus Museum ...
9.2/10 Wonderful! (31 reviews)
"Great stay with many amenities to enjoy within the building!"

Reviewed on Apr 3, 2026

Hyatus Luxury Residences City Crossing
See all properties in Cheshire
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.

Stay near popular Cheshire attractions

Roaring Brook Park

8.4/10 (12 reviews)
Explore the great outdoors at Roaring Brook Park, a lovely green space in Cheshire. Experience the area's entertainment venues and theater scene.
See properties

Cities near Cheshire

A mountainous landscape with dense forests, a small town, and a lake in the distance.

Southington

A church with a tall spire, surrounded by trees and a stone bridge.

Wallingford

A historic building with a clock tower, large columns, and a dome.

Hamden

A stone tower with American flags in front.

Meriden

Explore a world of travel with Expedia