Find Hotels with a Pool in Chester, VT

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Check availability on Chester Hotels with a Pool

Tonight
Dec 27 - Dec 28
Tomorrow
Dec 28 - Dec 29
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Our top choices for Chester hotels with a pool

Exterior
Historic 150-year-old farmhouse, Jacuzzi included

Historic 150-year-old farmhouse, Jacuzzi included

Historic 150-year-old farmhouse, Jacuzzi included
Chester Depot
9.8 out of 10, Exceptional, (10)
"This was a lovely inviting piece of history to stay in! The amenities were wonderful, the host very engaged with being sure we had what we needed. It is (for those who may not know Vermont) SUPER close to all sorts of hiking, tours, cute stores and great food! Our family will absolutely stay here again!"
United States
Amy S.
The price is ￥36,011
￥85,049 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Historic 150-year-old farmhouse, Jacuzzi included
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, (5)
"This was the perfect little getaway! Beautiful area, staff was nice, atmosphere was relaxing and having the hot tub option was perfect! "
United States
Harley
The price is ￥20,574
￥22,631 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Hideaway Inn Mt. Snow
Indoor pool, sun 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, (746)
"Spectular continental breakfast and really nice staff. Room was clean and beautiful. Amazing stay overall!"
United States
Jack
The price is ￥18,798
￥20,677 total
includes taxes & fees
Dec 31 - Jan 1, 2026
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 ￥23,750
￥26,126 total
includes taxes & fees
Jan 12 - Jan 13, 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, (968)
"Staff was very welcoming and the room was very clean. "
United States
Rebecca
The price is ￥19,361
￥21,006 total
includes taxes & fees
Dec 28 - Dec 29
Keene Elm City Hotel, an Ascend Collection Hotel
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 ￥22,918
￥25,209 total
includes taxes & fees
Jan 16 - Jan 17, 2026
Hampton Inn Brattleboro
Indoor pool, open 6:00 AM to 10:00 PM, sun 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 ￥21,703
￥23,549 total
includes taxes & fees
Dec 28 - Dec 29
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 ￥22,484
￥24,732 total
includes taxes & fees
Dec 31 - Jan 1, 2026
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, (359)
"Clean comfy nice staff "
United States
Katherine
The price is ￥25,876
￥28,076 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Hampton Inn & Suites Keene
Exterior
Black Mountain Inn

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (475)
"Clean, very friendly staff. Will stay again."
United States
Scot
The price is ￥15,500
￥17,050 total
includes taxes & fees
Dec 29 - Dec 30
Black Mountain Inn
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

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"10/10 Perfect Stay. So accommodating and kind staff. "
Angela 1-night trip
Posted 5 days ago
Kimpton Taconic Hotel 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. Kimpton Taconic Hotel by IHG: Provides complimentary bicycles, a seasonal outdoor pool, and a 24-hour fitness center. The Equinox Golf Resort & Spa: Features a seasonal outdoor pool, an indoor pool, and 4 restaurants. The Shire Woodstock: Features buffet, an indoor pool, and complimentary wired internet access.
What is there to see and do in Chester?
Explore places like Okemo Mountain Resort and Stratton Mountain Resort while you're in the area. Make a point to visit attractions like Bonnie's Bundles Dolls and DaVallia Art & Accents. Enjoy the choices of coffeehouses and restaurants in Chester, along with activities like skiing.
When is the best time to book a hotel with a pool in Chester?
Taking into account the local weather in Chester can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.