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

Indoor pool

Home2 Suites by Hilton East Haven New Haven

Home2 Suites by Hilton East Haven New Haven
3.0 star property
The Centre
9.6 out of 10, Exceptional, (549 reviews)
  • cleanliness
    Splash into relaxation at this East Haven retreat with a refreshing indoor pool escape.
The price is ￥22,161
￥25,485 total
includes taxes & fees
Jul 12 - Jul 13
Home2 Suites by Hilton East Haven New Haven
Free WiFi

Hampton Inn & Suites By Hilton North Haven

Hampton Inn & Suites By Hilton North Haven
2.5 star property
North Haven
9.6 out of 10, Exceptional, (35 reviews)
The price is ￥19,561
￥22,495 total
includes taxes & fees
Jun 24 - Jun 25
Hampton Inn & Suites By Hilton North Haven
Indoor pool

Baymont by Wyndham Branford/New Haven

Baymont by Wyndham Branford/New Haven
2.5 star property
Branford
6.6 out of 10, (1,003 reviews)
  • cleanliness
    Splash into serene seclusion at this Connecticut hotel with a private pool and sauna.
The price is ￥17,466
￥20,086 total
includes taxes & fees
Jun 25 - Jun 26
Baymont by Wyndham Branford/New Haven
Indoor pool

Wyndham Southbury

Wyndham Southbury
3.0 star property
Southbury
8.2 out of 10, Very Good, (1,225 reviews)
  • cleanliness
    Dive into refreshing year-round aquatics at this Southbury hotel, where the indoor pool beckons after a day of exploration.
The price is ￥16,353
￥18,806 total
includes taxes & fees
Jul 15 - Jul 16
Wyndham Southbury
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Heritage Hotel, Golf & Conference Center

Heritage Hotel, Golf & Conference Center
3.5 star property
Southbury
8.4 out of 10, Very Good, (1,017 reviews)
  • cleanliness
    Dive into saltwater serenity at this mountain spa retreat with indoor and seasonal outdoor pools.
The price is ￥19,530
￥25,225 total
includes taxes & fees
Jul 7 - Jul 8
Heritage Hotel, Golf & Conference Center
Indoor pool

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven
2.5 star property
West Haven
8.0 out of 10, Very Good, (1,663 reviews)
  • cleanliness
    Dive into this indoor pool paradise, just steps from New Haven's top attractions.
The price is ￥16,545
￥19,027 total
includes taxes & fees
Jun 21 - Jun 22
Best Western Executive Hotel Of New Haven - West Haven
Indoor pool, sun loungers

Inn at Middletown

Inn at Middletown
3.5 star property
Washington Street Historic District
9.0 out of 10, Wonderful, (611 reviews)
  • cleanliness
    Dive into poolside luxury in this historic hotel with a blissful indoor retreat and hot tub sanctuary.
The price is ￥28,088
￥35,507 total
includes taxes & fees
Jun 21 - Jun 22
Inn at Middletown
Indoor pool

Hilton Garden Inn Milford

Hilton Garden Inn Milford
3.0 star property
Milford
8.6 out of 10, Excellent, (1,043 reviews)
  • cleanliness
    Dive into a refreshing getaway at this hotel's spacious indoor pool sanctuary and fitness center.
The price is ￥18,597
￥21,387 total
includes taxes & fees
Jun 28 - Jun 29
Hilton Garden Inn Milford
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, (1,014 reviews)
  • cleanliness
    Dive into refreshing luxury at an indoor pool retreat where wellness meets comfort and convenience.
The price is ￥15,262
￥17,551 total
includes taxes & fees
Jul 5 - Jul 6
Best Western Plus New England Inn & Suites
Indoor pool

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, (842 reviews)
  • cleanliness
    Unwind in the indoor pool paradise while suburban comfort waits just outside your door.
The price is ￥20,903
￥24,039 total
includes taxes & fees
Jul 5 - Jul 6
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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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

Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent
"Clean room and pleasant staff. Very quiet stay. We would book again in the near future. The parking was a little tight on a Friday night."
Myrna 3-night trip
Posted 8 hours ago
Best Western Executive Hotel Of New Haven - West Haven

Frequently asked questions

What are some accommodations with pools in Cheshire?
Cheshire Welcome Inn: Hotel located near Lake Compounce. Features a snack bar/deli, a seasonal outdoor pool, and buffet. The Capitol Hotel: Features full, a pool, and free self parking. New Haven Hotel: Features complimentary wired internet access, an indoor pool, and free self parking. Holiday Inn Express Southington by IHG: Hotel located near Connecticut Convention Center. Offers buffet, a seasonal outdoor pool, and free self parking. Omni New Haven Hotel at Yale: Features a snack bar/deli, an indoor pool, and complimentary wired 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 Maplecroft Plaza Shopping Center, Cheshire Hollow Farm, and Bartlem Park 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.