Search Hotels with Pool in Chester

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Check availability on Chester Hotels with Pool

Tonight
24 Dec - 25 Dec
Tomorrow
25 Dec - 26 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Chester hotels with a pool

Indoor pool, pool loungers
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (742)
"Spectular continental breakfast and really nice staff. Room was clean and beautiful. Amazing stay overall!"
United States
Jack
The price is ฿3,662
฿4,028 total
includes taxes & fees
28 Dec - 29 Dec
Comfort Inn & Suites Brattleboro I-91
Indoor pool
Best Western Springfield Hotel

Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (806)
"so clean and friendly it was a perfect stay!"
United States
Colette
The price is ฿4,732
฿5,205 total
includes taxes & fees
7 Jan - 8 Jan 2026
Best Western Springfield Hotel
Indoor pool
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.4 out of 10, Very good, (967)
"The room was perfect, and the food was great "
United States
Paul
The price is ฿3,664
฿3,976 total
includes taxes & fees
28 Dec - 29 Dec
Keene Elm City Hotel, an Ascend Collection Hotel
Indoor pool, open 6:00 AM to 10:00 PM, pool loungers
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1001)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is ฿4,324
฿4,691 total
includes taxes & fees
25 Dec - 26 Dec
Best Western Plus Keene Hotel
Indoor pool
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
8.8 out of 10, Excellent, (1000)
"Very clean room, gentlemen at the front desk were welcoming and professional and the coffee was amazing! We are frequent visitors with you; we love IHG hotels. "
United States
Belinda
The price is ฿4,479
฿4,927 total
includes taxes & fees
28 Dec - 29 Dec
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Indoor pool
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (358)
"Clean comfy nice staff "
United States
Katherine
The price is ฿5,240
฿5,685 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Keene
Indoor pool
Hampton Inn Brattleboro

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (928)
"The room was very clean, and both staff and service were outstanding."
United States
Wonji
The price is ฿4,566
฿5,022 total
includes taxes & fees
2 Jan - 3 Jan 2026
Hampton Inn Brattleboro
Exterior
Black Mountain Inn

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (474)
"Clean, very friendly staff. Will stay again."
United States
Scot
The price is ฿3,080
฿3,388 total
includes taxes & fees
29 Dec - 30 Dec
Black Mountain Inn
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
10.0 out of 10, Exceptional, (4)
"Really happy with our stay and the way we felt at this hideaway "
United States
Edwin
The price is ฿4,204
฿4,624 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hideaway Inn Mt. Snow
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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Top Chester Hotel Reviews

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent
"I arrived far before published check-in time and only had to wait a reasonable amount of time to get into my room. Desk clerks were efficient and friendly. Clean, comfortable room. "
Wick 1-night trip
Posted 7 days ago
Comfort Inn & Suites Brattleboro I-91
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Super responsive staff, great accomodations "
Theresa 2-night trip
Posted 7 days ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Frequently asked questions

What are some hotels with pools in Chester?
Woodstock Inn & Resort: Features a seasonal outdoor pool, an indoor pool and 4 restaurants. Pointe at Castle Hill Resort: Offers a full-service spa, an indoor pool and free self parking. The Shire Woodstock: Resort, 3-minute walk from Mount Snow. Features a full-service spa, an outdoor pool and 2 hot tubs. Grand Summit Resort, A Vail Resorts Property: Offers a seasonal outdoor pool, an indoor pool and 4 restaurants. The Equinox Golf Resort & Spa: Features complimentary bicycles, a seasonal outdoor pool and a 24-hour fitness centre.
What is there to see and do in Chester?
Explore places such as Stratton Mountain Resort while you're in the area. Make a point to visit attractions such as Bonnie's Bundles Dolls and DaVallia Art & Accents. Enjoy the choices of coffee shops and restaurants in Chester, along with activities such as skiing.
When is the best time to book a hotel with a pool in Chester?
Taking the local weather in Chester into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chester are January, March, November and February, with each month seeing an average of 35 cm of snowfall.