Hotels with Pool & Resorts in Cheshire from AU$143

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Check availability on Cheshire Hotels with Pool

Tonight
5 Dec - 6 Dec
Tomorrow
6 Dec - 7 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Best Cheshire Hotels with Pool

Seasonal outdoor pool
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 star property
Southington
8.6 out of 10, Excellent, (1155)
"Staff is friendly room is clean. "
United States
Albana
The price is AU$143
includes taxes & fees
19 Dec - 20 Dec
Holiday Inn Express Southington by IHG
Pool
Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol

3.0 star property
Bristol
9.6 out of 10, Exceptional, (160)
"I would stay here again! "
United States
Jael
The price is AU$207
includes taxes & fees
21 Dec - 22 Dec
Home2 Suites by Hilton Bristol
Indoor pool
Hampton Inn by Hilton Shelton

Hampton Inn by Hilton Shelton

2.5 star property
Shelton
8.6 out of 10, Excellent, (1002)
"Convenient to Yale New Haven hospital. Nice room layout. Red Barn restaurant nearby great food and cocktails. Great breakfast at hotel"
United States
Carolyn
The price is AU$180
includes taxes & fees
2 Jan - 3 Jan 2026
Hampton Inn by Hilton Shelton
Fitness facility
Hyatt House Shelton

Hyatt House Shelton

3.0 star property
Shelton
8.4 out of 10, Very good, (1001)
"The staff was friendly, efficient and place was very family oriented "
United States
Michael
The price is AU$191
includes taxes & fees
7 Dec - 8 Dec
Hyatt House Shelton
Indoor pool
Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville

2.5 star property
Plainville
8.6 out of 10, Excellent, (908)
"Yes, the room was clean. Staff was very nice and we look forward to our next stay"
United States
Liza Marie
The price is AU$151
includes taxes & fees
28 Dec - 29 Dec
Fairfield Inn & Suites by Marriott Plainville
Indoor pool
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 AU$153
includes taxes & fees
14 Dec - 15 Dec
Best Western Plus New England Inn & Suites
Indoor pool
Hilton Garden Inn Milford

Hilton Garden Inn Milford

3.0 star property
Milford
8.4 out of 10, Very good, (1001)
"It was a nice stay for the price "
United States
karla
The price is AU$166
includes taxes & fees
18 Dec - 19 Dec
Hilton Garden Inn Milford
Indoor pool
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3.0 star property
Southington
8.2 out of 10, Very good, (1004)
"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 AU$179
includes taxes & fees
28 Dec - 29 Dec
Holiday Inn Cheshire - Southington by IHG
Indoor pool
Wyndham Southbury

Wyndham Southbury

3.0 star property
Southbury
8.2 out of 10, Very good, (1059)
"Nice room, friendly staff!"
United States
Scott
The price is AU$161
includes taxes & fees
11 Dec - 12 Dec
Wyndham Southbury
Indoor pool, pool loungers
Inn at Middletown

Inn at Middletown

3.5 star property
Washington Street Historic District
9.0 out of 10, Wonderful, (538)
"Clean room, friendly staff. "
United States
Katharine
Inn at Middletown
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

Hamden Hotel and Suites – Hamden New Haven

Hamden Hotel and Suites – Hamden New Haven

10/10 Excellent
"I really like this place!!!"
Nelson 1-night trip
Posted 3 days ago
Hamden Hotel and Suites – Hamden New Haven

Frequently asked questions

What are some accommodation options with pools in Cheshire?
Cheshire Welcome Inn: Offers a snack bar/deli, an indoor pool and complimentary high-speed (wired) Internet access. The Capitol Hotel: Provides buffet, an indoor pool and complimentary high-speed (wired) Internet access. Motel 6 New Haven - Branford, CT: Features buffet, a seasonal outdoor pool and free self parking. Cambria Hotel New Haven University Area: Provides full, a pool and free self parking. Extended Stay America Suites Hartford Farmington: Offers a snack bar/deli, a seasonal outdoor pool and buffet.
What is there to see and do in Cheshire?
Spend some time experiencing the great outdoors at Drazen Orchards and Bartlem Park. 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.