Search Hotels with Pool in Cheshire

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Check availability on Cheshire Hotels with Pool

Tonight
27 Dec - 28 Dec
Tomorrow
28 Dec - 29 Dec
Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan

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, (1182)
"Great breakfast, very clean, comfortable bed, very friendly staff."
United States
Megan
The price is ฿2,545
฿2,927 total
includes taxes & fees
2 Jan - 3 Jan 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, (1000)
"great stay."
United States
John
The price is ฿2,704
฿3,109 total
includes taxes & fees
2 Jan - 3 Jan 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, (173)
"Breakfast was easy and good options. "
United States
jessica
The price is ฿3,910
฿4,497 total
includes taxes & fees
4 Jan - 5 Jan 2026
Home2 Suites by Hilton Bristol
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, (1005)
"Very nice hotel clean friendly convenient location "
United States
Karen
The price is ฿3,028
฿3,483 total
includes taxes & fees
10 Jan - 11 Jan 2026
Hilton Garden Inn Milford
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 ฿3,283
฿4,311 total
includes taxes & fees
29 Dec - 30 Dec
Heritage Hotel, Golf, Spa & Conference Center
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 ฿3,259
฿3,747 total
includes taxes & fees
1 Jan - 2 Jan 2026
Fairfield Inn & Suites by Marriott Plainville
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, (1005)
"Pool was nice, breakfast was very good. "
United States
Matthew
The price is ฿3,197
฿3,676 total
includes taxes & fees
1 Jan - 2 Jan 2026
Holiday Inn Cheshire - Southington by IHG
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, (1000)
"Clean room, close to mamy amenities restaurants, bars, etc "
United States
Kerry- Ann
The price is ฿3,003
฿3,453 total
includes taxes & fees
25 Jan - 26 Jan 2026
Homewood Suites by Hilton Orange New Haven
Fitness facility
Hyatt House Shelton

Hyatt House Shelton

Hyatt House Shelton
3.0 star property
Shelton
8.4 out of 10, Very good, (1002)
"Place was great quiet and relaxing I enjoyed my time there thank you. "
United States
Jeanette
The price is ฿3,603
฿4,144 total
includes taxes & fees
29 Dec - 30 Dec
Hyatt House Shelton
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, (709)
"We had a wonderful stay; the staff were super friendly and the room was spotless. "
United States
ANDERSON
The price is ฿3,879
฿4,461 total
includes taxes & fees
2 Jan - 3 Jan 2026
Courtyard by Marriott Hartford Cromwell
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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Top Cheshire Hotel Reviews

Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

10/10 Excellent
"Place was very clean and well put together just in a bad area "
Olajuwon 1-night trip
Posted 6 days ago
Courtyard by Marriott Waterbury Downtown

Frequently asked questions

What are some accommodation options with pools in Cheshire?
Cheshire Welcome Inn: Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access. New Haven Hotel: Offers buffet, a pool and complimentary high-speed (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 with an outdoor swimming pool if you're planning to visit Cheshire in the hottest months of July, August or June, when the average temperature is 21°C. Accommodation with an indoor pool may be the way to go if you are visiting during the coldest months of January, February or December, when the average temp is 1°C.