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 16 - Sep 17
Tomorrow
Sep 17 - Sep 18
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

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 bar area with a white countertop, three brown bar stools, a mounted TV, and a liquor display cabinet.
A modern restaurant interior with a curved counter, seating area, and a wooden ceiling.
A modern restaurant with a wooden bar area, a long table with chairs, and a menu board.

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.
￥18,305
￥21,051 total
includes taxes & fees
Sep 27 - Sep 28
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, a convention center sign, and a parking garage entrance.
A modern bathroom with a glass shower enclosure, a toilet, a sink with a mirror, and a towel rack.
A hotel room with a large bed, a wooden nightstand, a TV, and a bathroom visible through an open door.

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.
￥14,241
￥16,377 total
includes taxes & fees
Sep 27 - Sep 28
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 spacious lobby with a stone wall, seating areas, a fireplace, and a kitchen in the background.
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.
￥22,770
￥26,186 total
includes taxes & fees
Sep 27 - Sep 28
Homewood Suites by Hilton Southington, CT
An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled deck.
A modern hotel lobby with a central bar area, refrigerated beverage dispensers, and a seating area with tables and chairs.
A hotel corridor with round tables, large windows, and a modern console table.
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.

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.
￥23,603
￥27,143 total
includes taxes & fees
Sep 27 - Sep 28
Hilton Garden Inn Wallingford/Meriden
An indoor swimming pool with clear water, tiled walls, and a 'No Diving' sign.
An outdoor patio area with a fire pit, seating, and a grill.
A hotel room with a dining table, chairs, a sofa, a TV, a fireplace, and a door.
A spacious room with a fireplace, a large dining table, multiple chairs, and a television mounted on the wall.

5. Residence Inn by Marriott Southington

Residence Inn by Marriott Southington
Southington
  • Indoor pool sanctuary offers year-round swimming at this fitness-focused hotel.
￥23,580
￥27,117 total
includes taxes & fees
Sep 27 - Sep 28
Residence Inn by Marriott Southington
An indoor swimming pool with clear blue water, surrounded by stone tiles and blue safety railings.
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 Best Western Plus hotel with a two-story structure, multiple parking spaces, and a landscaped front yard.
A spacious dining area with multiple tables and chairs, a kitchen in the background, and a modern ceiling design.

6. 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.
￥16,153
￥18,575 total
includes taxes & fees
Sep 21 - Sep 22
Best Western Plus New England Inn & Suites
A rectangular pool with metal railings, surrounded by lounge chairs and a brick building with multiple windows and balconies.
A spacious lobby with a high ceiling, a chandelier, a fireplace, and a dining area with tables and chairs.
A hotel room with two beds, a desk with a computer, a TV, and artwork on the wall.
Two white front-loading washing machines in a laundry area with a white tiled wall and a red baseboard.

7. Days Inn by Wyndham Berlin Meriden

Days Inn by Wyndham Berlin Meriden
Berlin
  • Dive into a refreshing getaway with this seasonal outdoor pool, where summertime relaxation meets comfortable accommodations.
￥11,384
￥13,091 total
includes taxes & fees
Sep 21 - Sep 22
Days Inn by Wyndham Berlin Meriden
A large indoor swimming pool with multiple seating areas and large windows.
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.
A modern hotel building with multiple floors and a prominent "HOME 2 SUITES BY HILTON" sign.

8. 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.
￥20,226
￥23,260 total
includes taxes & fees
Sep 27 - Sep 28
Home2 Suites by Hilton Bristol
A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a reception area.
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.
A modern lobby with a reception desk, seating area, and a large decorative 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.
￥25,174
￥28,950 total
includes taxes & fees
Sep 24 - Sep 25
DoubleTree by Hilton Hotel Bristol, Connecticut
A swimming pool with lounge chairs and tables, large windows, and a view of the outside.
A modern kitchen with a marble backsplash, stainless steel appliances, and dark cabinetry.
A spacious lobby with multiple seating areas, a large flat-screen TV, and a fireplace.
A modern kitchen with dark cabinetry, stainless steel appliances, a dining table with chairs, and pendant lighting.

10. 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.
￥27,148
￥31,221 total
includes taxes & fees
Sep 20 - Sep 21
Residence Inn by Marriott New Haven Hamden
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

Hilton Garden Inn Milford

Hilton Garden Inn Milford

10/10 Excellent
"Very clean hotel."
Erick 2-night trip
Posted 14 hours ago
Hilton Garden Inn Milford
Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

8/10 Good
"The carpet in the hallway looks old and dirty"
Josue A 4-night trip
Posted 16 hours ago
Hilton Garden Inn Shelton
Best Western Hartford Hotel & Suites

Best Western Hartford Hotel & Suites

10/10 Excellent
"Room was clean and had good AC."
Megan 1-night trip
Posted 1 day ago
Best Western Hartford Hotel & Suites
La Quinta Inn & Suites by Wyndham New Haven

La Quinta Inn & Suites by Wyndham New Haven

10/10 Excellent
"Gooo"
Victor 1-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham New Haven
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

10/10 Excellent
"Very clean hotel."
Maria 1-night trip
Posted 2 days ago
Holiday Inn Express Southington by IHG
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

10/10 Excellent
"Friendly staff"
Miguel 1-night trip
Posted 3 days ago
Hyatt Place Milford / New Haven

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: Hotel located near The Meadows Music Theatre. 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, 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 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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