Find Family Hotels in Cheshire, CT

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Cheshire Family Hotels

Our top choices for Cheshire family-friendly hotels

Reception
Spark by Hilton Guilford

Spark by Hilton Guilford

Spark by Hilton Guilford
2.5 star property
Guilford
8.8 out of 10, Excellent, (64)
"Good clean property with great staff "
United States
David
The price is NT$3,121
NT$3,589 total
includes taxes & fees
Jan 3 - 2026/1/4
Spark by Hilton Guilford
Exterior detail
New Haven Hotel

New Haven Hotel

New Haven Hotel
3.5 star property
Downtown New Haven
9.0 out of 10, Wonderful, (1921)
"Very nice hotel. "
United States
REINA
The price is NT$3,553
NT$4,086 total
includes taxes & fees
Dec 25 - Dec 26
New Haven Hotel
Exterior
Best Western Plus New England Inn & Suites

Best Western Plus New England Inn & Suites

Best Western Plus New England Inn & Suites
2.5 star property
Berlin
8.6 out of 10, Excellent, (1003)
"great stay."
United States
John
The price is NT$2,718
NT$3,125 total
includes taxes & fees
Jan 2 - 2026/1/3
Best Western Plus New England Inn & Suites
Exterior
Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford
2.5 star property
East Hartford
9.0 out of 10, Wonderful, (1072)
"Wonderful place to stay"
United States
Margarita
The price is NT$2,970
NT$3,415 total
includes taxes & fees
Dec 20 - Dec 21
Hampton Inn & Suites Hartford/East Hartford
Lobby
Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown
3.0 star property
Waterbury
8.4 out of 10, Very Good, (1062)
"Everything was great 👍 "
United States
Janet
The price is NT$2,776
NT$3,193 total
includes taxes & fees
Dec 14 - Dec 15
Courtyard by Marriott Waterbury Downtown
Exterior
Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (165)
"I would stay here again! "
United States
Jael
The price is NT$3,719
NT$4,276 total
includes taxes & fees
Dec 21 - Dec 22
Home2 Suites by Hilton Bristol
Exterior
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG
3.0 star property
Southington
8.2 out of 10, Very Good, (1002)
"Highly recommend staying here. The rooms are clean and the staff go above and beyond to make sure that guests have a comfortable stay."
United States
Veronica
The price is NT$2,839
NT$3,265 total
includes taxes & fees
Dec 25 - Dec 26
Holiday Inn Cheshire - Southington by IHG
Exterior
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area
3.0 star property
West River
8.8 out of 10, Excellent, (989)
"Room was clean hotel was very updated and nice as well. "
United States
Talicia
The price is NT$3,301
NT$3,797 total
includes taxes & fees
Jan 4 - 2026/1/5
Cambria Hotel New Haven University Area
Desk, laptop workspace, blackout drapes, iron/ironing board
The Capitol Hotel

The Capitol Hotel

The Capitol Hotel
3.0 star property
Downtown Hartford
7.6 out of 10, Good, (1105)
"It was clean and the check in was easy."
United States
SHAWN
The price is NT$2,502
NT$2,877 total
includes taxes & fees
Dec 14 - Dec 15
The Capitol Hotel
Lobby
Days Inn by Wyndham Southington

Days Inn by Wyndham Southington

Days Inn by Wyndham Southington
2.0 star property
Southington
7.4 out of 10, Good, (1001)
"Staff was so friendly and check in was a breeze. Looks like they are doing really nice renovations. Travel for business and the do charge a reasonable fee for dogs but worth it. Will be staying again. "
United States
Lisa
The price is NT$2,496
NT$2,870 total
includes taxes & fees
Dec 13 - Dec 14
Days Inn by Wyndham Southington
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.
View all properties

Top Cheshire Hotel Reviews

Best Western Hartford Hotel & Suites

Best Western Hartford Hotel & Suites

10/10 Excellent
"Great, no problems. Staff professional "
John 1-night trip
Posted 1 day ago
Best Western Hartford Hotel & Suites

Explore a world of travel with Expedia

Frequently asked questions

What's Cheshire like for family-friendly vacations?
You might want to consider the historic destination of Cheshire if you've been thinking about a trip for the whole family. The beautiful waterfalls, forests, and restaurants are just a few things that make this an attractive spot for a family vacation. Take to the air and fly into Oxford, CT (OXC-Waterbury - Oxford), which is located 12 mi (19.3 km) from the city center.
When's the best time to book a family-friendly vacation in Cheshire?
The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 33°F. Average annual precipitation for Cheshire is 54 inches.
What's there to see and do with your family in Cheshire?
Cheshire Hollow Farm and Maplecroft Plaza Shopping Center are interesting attractions you and your family might enjoy exploring while you are staying in Cheshire. Make sure you have lots of time for activities like Mount Southington Ski Area and Toyota Oakdale Theatre.