A stone tower with a metal gate, surrounded by trees and a stone wall.

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Check availability on Cheshire Hotels with a Pool

Tonight
Sep 29 - Sep 30
Tomorrow
Sep 30 - Oct 1
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Cheshire hotels with a pool

An indoor swimming pool with a lifeguard warning sign, chairs, and a view of the outside.
A modern restaurant with a wooden bar area, a long table with chairs, and a menu board.
A modern restaurant interior with a curved counter, seating area, and a wooden ceiling.
A modern bar area with a white countertop, three brown bar stools, a mounted TV, and a liquor display cabinet.

1. Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG
Southington
  • Refreshing indoor pool haven with treadmills and fitness center for year-round aquatic escapes.
₩153,010
₩175,962 total
includes taxes & fees
Oct 25 - Oct 26
Holiday Inn Cheshire - Southington by IHG
A poolside wheelchair by a pool with lounge chairs and a potted plant in the background.
A modern building with a large digital welcome sign and a clear sky.
A hotel room with a large bed, a wooden nightstand, a TV, and a bathroom visible through an open door.
A coffee station with two coffee machines, a coffee press, and various coffee pods and cups.

2. Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG
Southington
  • Immerse in the refreshing seasonal outdoor pool, a perfect summertime retreat with convenient morning to evening hours.
₩124,304
₩142,950 total
includes taxes & fees
Oct 4 - Oct 5
Holiday Inn Express Southington by IHG
A large indoor swimming pool with a 'No Diving' sign, surrounded by lounge chairs and a tiled floor.
A hotel with multiple floors, a central entrance, and a well-maintained lawn.
A modern lobby with a fireplace, comfortable seating, and framed pictures on the walls.
An outdoor patio with a fire pit, wicker furniture, and a pergola structure.

3. Homewood Suites by Hilton Southington, CT

Homewood Suites by Hilton Southington, CT
Southington
  • Splash into aquatic bliss at this indoor pool retreat, where sun loungers await for ultimate relaxation.
₩198,750
₩228,562 total
includes taxes & fees
Oct 25 - Oct 26
Homewood Suites by Hilton Southington, CT
An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled deck.
A modern living room with a flat-screen TV, a red armchair, a grey sofa, a wooden entertainment unit, and a large window with curtains.
A hotel corridor with round tables, large windows, and a modern console table.
A modern hotel lobby with a central bar area, refrigerated beverage dispensers, and a seating area with tables and chairs.

4. Hilton Garden Inn Wallingford/Meriden

Hilton Garden Inn Wallingford/Meriden
Wallingford
  • Dive into year-round aquatic bliss at this hotel's pristine indoor pool sanctuary.
₩204,302
₩234,947 total
includes taxes & fees
Oct 25 - Oct 26
Hilton Garden Inn Wallingford/Meriden
An indoor swimming pool with clear blue water, surrounded by stone tiles and blue safety railings.
A spacious dining area with multiple tables and chairs, a kitchen in the background, and a modern ceiling design.
A hotel room with a bed, bedside tables, a desk, a TV, a large mirror, a bathroom with a bathtub, and a striped carpet.
A hotel lobby with a gray sofa, a round table, a reception desk, a TV, and a kitchen area in the background.

5. Best Western Plus New England Inn & Suites

Best Western Plus New England Inn & Suites
Berlin
  • Dive into refreshing luxury at an indoor pool retreat where wellness meets comfort and convenience.
₩141,798
₩163,068 total
includes taxes & fees
Oct 12 - Oct 13
Best Western Plus New England Inn & Suites
A swimming pool with lounge chairs and tables, large windows, and a view of the outside.
A modern kitchen with dark cabinetry, stainless steel appliances, a dining table with chairs, and pendant lighting.
An outdoor patio area with a stone fire pit, wicker furniture, and a bar area with a flat-screen TV.
A spacious lobby with multiple seating areas, a large flat-screen TV, and a fireplace.

6. Residence Inn by Marriott New Haven Hamden

Residence Inn by Marriott New Haven Hamden
Hamden
  • Swim year-round in this hotel's inviting indoor pool, steps from comfy outdoor patios.
₩195,631
₩224,975 total
includes taxes & fees
Oct 4 - Oct 5
Residence Inn by Marriott New Haven Hamden
A large indoor swimming pool with multiple seating areas and large windows.
A modern lounge with a pool table, comfortable seating, and a large window offering a view of the outdoors.
A modern breakfast area with a counter, seating, and a refrigerator.
An outdoor seating area with sofas and chairs, a glass-top table with a fire feature, and yellow chairs in the background.

7. Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
Bristol
  • Serene hotel with an indoor pool escape just steps away from relaxing in a soothing hot tub.
₩187,647
₩215,794 total
includes taxes & fees
Oct 18 - Oct 19
Home2 Suites by Hilton Bristol
An indoor swimming pool with clear water, tiled walls, and a 'No Diving' sign.
A hotel room with a dining table, chairs, a sofa, a TV, a fireplace, and a door.
A hotel room with a sofa, a desk with a computer, a TV, a dining table with chairs, and a lamp.
An outdoor patio area with a fire pit, seating, and a grill.

8. Residence Inn by Marriott Southington

Residence Inn by Marriott Southington
Southington
  • Indoor pool sanctuary offers year-round swimming at this fitness-focused hotel.
₩230,192
₩264,720 total
includes taxes & fees
Oct 25 - Oct 26
Residence Inn by Marriott Southington
A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a reception area.
A modern lobby with a reception desk, seating area, and a large decorative light fixture.
An outdoor seating area with fire pits and umbrellas, surrounded by modern buildings with large windows.
A modern hotel lobby with a central island, red chairs, a marble countertop, and a large overhead light fixture.

9. DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut
Bristol
  • Serene indoor saltwater pool retreat creates an oasis of relaxation with a nearby hot tub in this upscale Connecticut hotel.
₩220,957
₩254,101 total
includes taxes & fees
Oct 5 - Oct 6
DoubleTree by Hilton Hotel Bristol, Connecticut
An indoor swimming pool with a 'No Diving' sign, a glass enclosure, and a tiled wall with a 'No Diving' sign.
A hotel room with a sofa, two small tables, a TV, a desk, and a mirror.
A lobby with a blue sofa, a small round table, and a fireplace.
A Fairfield Inn & Suites hotel with a large parking lot and snow-covered ground.

10. Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
Plainville
  • Swim year-round at this hotel's indoor pool, with 24-hour fitness center just steps away.
₩154,223
₩177,357 total
includes taxes & fees
Oct 4 - Oct 5
Fairfield Inn & Suites by Marriott Plainville
View all properties

Choose what matters most at hotels with a pool in Cheshire

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Cheshire Hotel Reviews

Best Western Hartford Hotel & Suites

Best Western Hartford Hotel & Suites

10/10 Excellent
"I"
Jeremie 1-night trip
Posted 9 hours ago
Best Western Hartford Hotel & Suites
Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

8/10 Good
"The hotel is being redecorated and I don’t think our room was finished (trim etc), but it should be nice when finished. The shower started with ice cold water for 5+ minutes until it finally got warm. Sketchy area: parking lot sign says you assume the risk, and lobby has a Security guy at night. We needed another remote for the tv to stream our shows and the front desk couldn’t help with that. Housekeeping skipped our room. But a good deal for the price: our King studio was spacious, everything clean, and the free breakfast - eggs, waffles, oatmeal, bananas etc - was excellent. I’d try this hotel again."
Ruth 2-night trip
Posted 19 hours ago
Hampton Inn & Suites Hartford/East Hartford
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent
"Always a great stay!! Thank you for always being nice and helpful!"
Jenna 1-night trip
Posted 22 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: Features a snack bar/deli, a seasonal outdoor pool, and buffet. The Capitol Hotel: Hotel located near PeoplesBank Arena. Offers buffet, an indoor pool, and complimentary wired internet access. New Haven Hotel: Offers full, a pool, and free self parking. Holiday Inn Express Southington by IHG: Provides a snack bar/deli, an indoor pool, and complimentary wired internet access. Hampton Inn & Suites Hartford/East Hartford: Hotel located near PeoplesBank Arena. Features buffet, 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 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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