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

Find Hotels with a Pool in Cheshire, CT

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check availability on Cheshire Hotels with a Pool

Tonight
Aug 13 - Aug 14
Tomorrow
Aug 14 - Aug 15
This weekend
Aug 14 - Aug 16
Next weekend
Aug 21 - Aug 23

Our top choices for Cheshire hotels with a pool

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.
₩171,469
₩197,189 total
includes taxes & fees
Sep 6 - Sep 7
Holiday Inn Cheshire - Southington by IHG

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.
₩129,667
₩149,118 total
includes taxes & fees
Aug 16 - Aug 17
Holiday Inn Express Southington by IHG

3. 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.
₩195,744
₩225,105 total
includes taxes & fees
Sep 7 - Sep 8
Hilton Garden Inn Wallingford/Meriden

4. Homewood Suites by Hilton Wallingford-Meriden

Homewood Suites by Hilton Wallingford-Meriden
Wallingford
  • Splash into fun at this hotel with an indoor pool, fitness center, and nearby skiing trails.
₩202,906
₩233,342 total
includes taxes & fees
Sep 7 - Sep 8
Homewood Suites by Hilton Wallingford-Meriden

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.
₩147,917
₩170,105 total
includes taxes & fees
Aug 19 - Aug 20
Best Western Plus New England Inn & Suites

6. Residence Inn by Marriott Southington

Residence Inn by Marriott Southington
Southington
  • Indoor pool sanctuary offers year-round swimming at this fitness-focused hotel.
₩210,463
₩242,032 total
includes taxes & fees
Aug 16 - Aug 17
Residence Inn by Marriott Southington

7. 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.
₩208,002
₩239,202 total
includes taxes & fees
Sep 6 - Sep 7
DoubleTree by Hilton Hotel Bristol, Connecticut

8. 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.
₩105,857
₩121,736 total
includes taxes & fees
Sep 7 - Sep 8
Days Inn by Wyndham Berlin Meriden

9. 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.
₩201,030
₩231,185 total
includes taxes & fees
Sep 7 - Sep 8
Home2 Suites by Hilton Bristol

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.
₩251,425
₩289,139 total
includes taxes & fees
Aug 16 - Aug 17
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

Courtyard by Marriott New Haven Orange-Milford

Courtyard by Marriott New Haven Orange-Milford

10/10 Excellent
"Excellent, simple, dining facilities that gave us an opportunity to have a small but good dinner and an interesting breakfast without relieving the facility. It was a bit of aExcellent, simple, dining facilities that gave us an opportunity to have a small but good dinner and an interesting breakfast without relieving the facility. It was a bit of a surprise surprise"
Allan 1-night trip
Posted 5 hours ago
Courtyard by Marriott New Haven Orange-Milford
Best Western Hartford Hotel & Suites

Best Western Hartford Hotel & Suites

10/10 Excellent
"Was very nice, the staff is fine."
Amauris 2-night trip
Posted 13 hours ago
Best Western Hartford Hotel & Suites
Hilton Garden Inn Milford

Hilton Garden Inn Milford

10/10 Excellent
"Loved the pool!"
Steven 1-night trip
Posted 1 day ago
Hilton Garden Inn Milford
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

8/10 Good
"It was ok a little dated breakfast was pretty good coffee was excellent ..."
Mickey 2-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
"I felt happy the moment I checked in. Spacious clean room with wetbar, great view to back of property, housekeeping provided daily all essentials. Breakfast was great, plenty of parking, great interaction with staff"
SILKE 3-night trip
Posted 2 days ago
Hyatt Place Milford / New Haven

Frequently asked questions

What are some accommodations with pools in Cheshire?
Cheshire Welcome Inn: Provides a snack bar/deli, a seasonal outdoor pool, and buffet. Motel 6 New Haven - Branford, CT: Features full, a pool, and free self parking. Holiday Inn Express Southington by IHG: Hotel located near Connecticut Convention Center. Features buffet, a seasonal outdoor pool, and free self parking. Best Western Executive Hotel Of New Haven - West Haven: Offers complimentary wired internet access, an indoor pool, and free self parking. Omni New Haven Hotel at Yale: 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 Drazen Orchards and Bartlem Park. Discover sights such as Maplecroft Plaza Shopping Center, Barker Character, Comic and Cartoon Museum, and Roaring Brook 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.

Explore a world of travel with Expedia