Find Hotels with a Pool 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 Hotels with a Pool

Tonight
Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Cheshire hotels with a pool

Seasonal outdoor pool
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG
2.5 star property
Southington
8.6 out of 10, Excellent, (1185)
"Great breakfast, very clean, comfortable bed, very friendly staff."
United States
Megan
The price is ₩119,658
₩137,607 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Express Southington by IHG
Indoor pool
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, (1004)
"great stay."
United States
John
The price is ₩125,597
₩144,436 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Best Western Plus New England Inn & Suites
Pool
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, (174)
"Breakfast was easy and good options. "
United States
jessica
The price is ₩181,649
₩208,897 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Home2 Suites by Hilton Bristol
View from property
Heritage Hotel, Golf, Spa & Conference Center

Heritage Hotel, Golf, Spa & Conference Center

Heritage Hotel, Golf, Spa & Conference Center
3.5 star property
Southbury
8.4 out of 10, Very Good, (1002)
"Very lovely hotel "
United States
Nancy M
The price is ₩152,499
₩200,242 total
includes taxes & fees
Dec 30 - Dec 31
Heritage Hotel, Golf, Spa & Conference Center
Indoor pool
Hilton Garden Inn Milford

Hilton Garden Inn Milford

Hilton Garden Inn Milford
3.0 star property
Milford
8.4 out of 10, Very Good, (1006)
"Very nice hotel clean friendly convenient location "
United States
Karen
The price is ₩140,677
₩161,779 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Hilton Garden Inn Milford
Indoor pool
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, (1009)
"Pool was nice, breakfast was very good. "
United States
Matthew
The price is ₩132,633
₩152,528 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Cheshire - Southington by IHG
Indoor pool
Courtyard by Marriott Hartford Cromwell

Courtyard by Marriott Hartford Cromwell

Courtyard by Marriott Hartford Cromwell
3.0 star property
Cromwell
8.6 out of 10, Excellent, (710)
"Front desk staff were great!"
United States
Lucy
The price is ₩180,208
₩207,239 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Courtyard by Marriott Hartford Cromwell
Indoor pool
Homewood Suites by Hilton Orange New Haven

Homewood Suites by Hilton Orange New Haven

Homewood Suites by Hilton Orange New Haven
3.0 star property
Orange
9.2 out of 10, Wonderful, (1002)
"Clean room, close to mamy amenities restaurants, bars, etc "
United States
Kerry- Ann
The price is ₩139,495
₩160,419 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Homewood Suites by Hilton Orange New Haven
Outdoor pool
Avon Old Farms Hotel

Avon Old Farms Hotel

Avon Old Farms Hotel
3.5 star property
Avon
8.4 out of 10, Very Good, (1001)
"Very nice place to stay"
United States
Alvero
The price is ₩142,724
₩195,633 total
includes taxes & fees
Dec 30 - Dec 31
Avon Old Farms Hotel
Indoor pool
Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
2.5 star property
Plainville
8.6 out of 10, Excellent, (914)
"Great place stayed several times."
United States
Marlene D
The price is ₩151,374
₩174,080 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Fairfield Inn & Suites by Marriott Plainville
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

Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

10/10 Excellent
"Excellent breakfast. Comfortable beds and large bathroom."
Amy 1-night trip
Posted 4 days ago
Hampton Inn & Suites Hartford/East Hartford

Frequently asked questions

What are some accommodations with pools in Cheshire?
Cheshire Welcome Inn: Offers buffet, an indoor pool, and complimentary wired internet access. New Haven Hotel: Offers buffet, a pool, and complimentary wired internet access. The Capitol Hotel: Offers a snack bar/deli, an indoor pool, and free self parking. Cambria Hotel New Haven University Area: Offers a snack bar/deli, a seasonal outdoor pool, and buffet. Hampton Inn & Suites Hartford/East Hartford: Provides free self parking, an indoor pool, and complimentary wireless internet access.
What is there to see and do in Cheshire?
Spend some time experiencing the great outdoors at Roaring Brook Park and Drazen Orchards. Discover sights such as Barker Character, Comic and Cartoon Museum, Cheshire Hollow Farm, and Maplecroft Plaza Shopping Center during your stay. You'll also discover lots of options for restaurants in Cheshire.
When is the best time to book a hotel with a pool in Cheshire?
You may want to consider a place to stay that has an outdoor pool if you will be visiting Cheshire in the hottest months of July, August, or June when the average temperature is 70°F. Lodging with an indoor pool may be the way to go if you come to town during the coldest months of January, February, or December when the average temp is 33°F.