The Best Hotels with a Pool in Cheshire, CT from AED 312 in 2026

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Check availability on Cheshire Hotels with a Pool

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Our top choices for Cheshire hotels with a pool

1. Holiday Inn Cheshire - Southington by IHG

Southington

Refreshing indoor pool haven with treadmills and fitness center for year-round aquatic escapes.

AED 400

AED 460 total

includes taxes & fees

25 Oct - 26 Oct

Premium bedding, down comforters, pillowtop beds, desk

2. Holiday Inn Express Southington by IHG

Southington

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

AED 337

AED 388 total

includes taxes & fees

4 Oct - 5 Oct

Suite, 1 King Bed, Non Smoking, Jetted Tub | Desk, blackout drapes, iron/ironing board, cribs (free)

3. Best Western Plus New England Inn & Suites

Berlin

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

AED 385

AED 442 total

includes taxes & fees

1 Oct - 2 Oct

4. Hilton Garden Inn Wallingford/Meriden

Wallingford

Dive into year-round aquatic bliss at this hotel's pristine indoor pool sanctuary.

AED 554

AED 637 total

includes taxes & fees

4 Oct - 5 Oct

Indoor pool, open 8:00 AM to 9:00 PM, sun loungers

5. Homewood Suites by Hilton Southington, CT

Southington

Splash into aquatic bliss at this indoor pool retreat, where sun loungers await for ultimate relaxation.

AED 592

AED 681 total

includes taxes & fees

5 Oct - 6 Oct

Room, 2 Queen Beds, Non Smoking | Premium bedding, desk, blackout drapes, iron/ironing board

6. Days Inn by Wyndham Berlin Meriden

Berlin

Dive into a refreshing getaway with this seasonal outdoor pool, where summertime relaxation meets comfortable accommodations.

AED 271

AED 312 total

includes taxes & fees

11 Oct - 12 Oct

Premium bedding, pillowtop beds, in-room safe, desk

7. Residence Inn by Marriott Southington

Southington

Indoor pool sanctuary offers year-round swimming at this fitness-focused hotel.

AED 591

AED 680 total

includes taxes & fees

4 Oct - 5 Oct

8. Home2 Suites by Hilton Bristol

Bristol

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

AED 506

AED 582 total

includes taxes & fees

4 Oct - 5 Oct

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Choose what matters most at hotels with a pool in Cheshire

Breakfast included

Hot tub

4 stars

5 stars

Spa

Top Cheshire Hotel Reviews

Wyndham Southbury

8/10 Good

"Extra for microwave in room so if you want one be sure to book with it."

Hilton Garden Inn Milford

10/10 Excellent

"Great stay"

Hyatt Place Milford / New Haven

10/10 Excellent

"I love the fresh cut up fruits for breakfast. Microwave is not available in our room. The electrical socket near the tv was not working. Construction noises woke me up. Other than those small little things everything was perfect."

Hilton Garden Inn Shelton

10/10 Excellent

"Smelled clean, clean rooms and property, nice staff."

Frequently asked questions

What are some accommodations with pools in Cheshire?

Cheshire Welcome Inn: Features full, a pool, and free self parking. The Capitol Hotel: Offers a snack bar/deli, a seasonal outdoor pool, and buffet. New Haven Hotel: Features buffet, an indoor pool, and complimentary wired internet access. Best Western Executive Hotel Of New Haven - West Haven: Offers a snack bar/deli, an indoor pool, and complimentary wired internet access. Holiday Inn Express Southington by IHG: Provides complimentary wired internet access, an indoor pool, and free self parking.

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 Maplecroft Plaza Shopping Center, Cheshire Hollow Farm, and Barker Character, Comic and Cartoon Museum 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.

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Check availability on Cheshire Hotels with a Pool

Our top choices for Cheshire hotels with a pool

1. Holiday Inn Cheshire - Southington by IHG

2. Holiday Inn Express Southington by IHG