Find Hotels with a Pool in Cheshire, CT

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Check availability on Cheshire Hotels with a Pool

Our top choices for Cheshire hotels with a pool

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, (164)
"I would stay here again! "
United States
Jael
The price is AED 438
AED 503 total
includes taxes & fees
21 Dec - 22 Dec
Home2 Suites by Hilton Bristol
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, (1003)
"great stay."
United States
John
The price is AED 320
AED 368 total
includes taxes & fees
2 Jan - 3 January 2026
Best Western Plus New England Inn & Suites
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, (1163)
"Clean rooms, Good breakfast, Solid Coffee"
United States
Anthony
The price is AED 290
AED 334 total
includes taxes & fees
28 Dec - 29 Dec
Holiday Inn Express Southington by IHG
Indoor pool
Hampton Inn & Suites New Haven - South - West Haven

Hampton Inn & Suites New Haven - South - West Haven

Hampton Inn & Suites New Haven - South - West Haven
2.5 star property
West Haven
8.4 out of 10, Very Good, (1001)
"always a very friendly front desk and the location is convenient "
United States
Melissa
The price is AED 317
AED 364 total
includes taxes & fees
20 Dec - 21 Dec
Hampton Inn & Suites New Haven - South - West Haven
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, (1002)
"It was a nice stay for the price "
United States
karla
The price is AED 326
AED 375 total
includes taxes & fees
20 Dec - 21 Dec
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, (1001)
"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 AED 334
AED 384 total
includes taxes & fees
25 Dec - 26 Dec
Holiday Inn Cheshire - Southington by IHG
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, (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 AED 320
AED 367 total
includes taxes & fees
28 Dec - 29 Dec
Fairfield Inn & Suites by Marriott Plainville
Indoor pool
Wyndham Southbury

Wyndham Southbury

Wyndham Southbury
3.0 star property
Southbury
8.2 out of 10, Very Good, (1064)
"Nice room, friendly staff!"
United States
Scott
The price is AED 340
AED 391 total
includes taxes & fees
17 Dec - 18 Dec
Wyndham Southbury
Fitness facility
Hyatt House Shelton

Hyatt House Shelton

Hyatt House Shelton
3.0 star property
Shelton
8.4 out of 10, Very Good, (1002)
"Always a pleasure to stay here 1s a year keep coming back!!"
United States
Mark
The price is AED 403
AED 463 total
includes taxes & fees
13 Dec - 14 Dec
Hyatt House Shelton
Indoor pool
Hampton Inn & Suites Rocky Hill - Hartford South

Hampton Inn & Suites Rocky Hill - Hartford South

Hampton Inn & Suites Rocky Hill - Hartford South
2.5 star property
Rocky Hill
9.2 out of 10, Wonderful, (766)
"Very clean hotel and the lobby felt very welcoming. The breakfast was great! "
United States
Amy
The price is AED 408
AED 470 total
includes taxes & fees
4 Jan - 5 January 2026
Hampton Inn & Suites Rocky Hill - Hartford South
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

Wyndham Southbury

Wyndham Southbury

10/10 Excellent
"Little dated but very nice for the price."
Anthony 1-night trip
Posted 1 day ago
Wyndham Southbury

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Frequently asked questions

What are some accommodations with pools in Cheshire?
Cheshire Welcome Inn: Offers a snack bar/deli, a seasonal outdoor pool, and buffet. New Haven Hotel: Features buffet, an indoor pool, and complimentary wired internet access. The Capitol Hotel: Provides a snack bar/deli, an indoor pool, and complimentary wired internet access. Cambria Hotel New Haven University Area: Offers a snack bar/deli, an indoor pool, and free self parking. Holiday Inn Express Southington by IHG: Features buffet, a pool, and complimentary wired internet access.
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 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.