TOP Hotels with Swimming Pool in Cheshire, CT for 2026

Q: What are some accommodation options with pools in Cheshire?

Cheshire Welcome Inn : Offers a snack bar/deli, a seasonal outdoor pool and buffet. New Haven Hotel : Offers complimentary high-speed (wired) Internet access, an indoor pool and free self parking. The Capitol Hotel : Features full, a pool and free self parking. Omni New Haven Hotel at Yale : Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access. Holiday Inn Express Southington by IHG : Provides a snack bar/deli, a seasonal outdoor pool and free self parking.

Castle Craig at Hubbard Park, Meriden, CT. easily replaceable sky. with a clean, classic view of the tower. Very recognizable image of this historic structure.

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Our top choices for Cheshire hotels with a pool

Home2 Suites by Hilton Bristol

Bristol

Serene hotel with an indoor pool escape just steps away from relaxing in a soothing hot tub.

₹14,736 total

includes taxes & fees

26 May - 27 May

Hampton Inn & Suites By Hilton North Haven

North Haven

₹14,828 total

includes taxes & fees

19 May - 20 May

Wyndham Southbury

Southbury

Dive into refreshing year-round aquatics at this Southbury hotel, where the indoor pool beckons after a day of exploration.

₹10,113 total

includes taxes & fees

26 May - 27 May

Indoor pool, seasonal outdoor pool, pool umbrellas, pool loungers

Heritage Hotel, Golf & Conference Center

Southbury

Dive into saltwater serenity at this mountain spa retreat with indoor and seasonal outdoor pools.

₹16,275 total

includes taxes & fees

10 May - 11 May

Holiday Inn Express Southington by IHG

Southington

Immerse in the refreshing seasonal outdoor pool, a perfect summertime retreat with convenient morning to evening hours.

₹11,783 total

includes taxes & fees

26 May - 27 May

Inn at Middletown

Washington Street Historic District

Dive into poolside luxury in this historic hotel with a blissful indoor retreat and hot tub sanctuary.

₹20,112 total

includes taxes & fees

7 May - 8 May

Best Western Plus New England Inn & Suites

Berlin

Dive into refreshing luxury at an indoor pool retreat where wellness meets comfort and convenience.

₹9,990 total

includes taxes & fees

10 May - 11 May

Best Western Executive Hotel Of New Haven - West Haven

West Haven

Dive into this indoor pool paradise, just steps from New Haven's top attractions.

₹12,391 total

includes taxes & fees

2 Jun - 3 Jun

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Choose what matters most at hotels with a pool in Cheshire

Breakfast included

Hot tub

Top Cheshire Hotel Reviews

Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent

"Rooms and property were clean… the breakfast bread set up was good… just was cold"

Hilton Garden Inn Shelton

4/10 Poor

"Hotel is very outdated. Walls and carpets dirty, outlet covers are filthy. Shower fixtures are rusty. Pool had no towels despite multiple guests informing the staff. WiFi did not recognize last name and room number to log in. Toilet seat very loose. And to top it off, alarm in room went off at 6am (not set by us!). Will not stay at a Hilton again. Sticking to Marriots in the future. "

La Quinta Inn & Suites by Wyndham New Haven

2/10 Terrible

"Room was decent however the bathroom and tub and floor tile especially were dated and OLD. Thank goodness it was just one night - could not step into that bathtub. Fri night- highway traffic was noisy so rooms definitely could use sound proofing. Do not recommend staying. Lobby and breakfast areas were nice. "

Frequently asked questions

What are some accommodation options with pools in Cheshire?

Cheshire Welcome Inn: Offers a snack bar/deli, a seasonal outdoor pool and buffet. New Haven Hotel: Offers complimentary high-speed (wired) Internet access, an indoor pool and free self parking. The Capitol Hotel: Features full, a pool and free self parking. Omni New Haven Hotel at Yale: Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access. Holiday Inn Express Southington by IHG: Provides a snack bar/deli, a seasonal outdoor pool and free self parking.

What is there to see and do in Cheshire?

Spend some time experiencing the great outdoors at Bartlem Park and Roaring Brook Park. Discover sights such as Maplecroft Plaza Shopping Center, Barker Character, Comic and Cartoon Museum and Cheshire Hollow Farm 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.

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