Find Hotels with a Pool in Chester, VT

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Check availability on Chester Hotels with a Pool

Our top choices for Chester hotels with a pool

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, (740)
"Price, clean and spacious room, comfy bed."
United States
June
The price is NT$3,486
NT$3,834 total
includes taxes & fees
Dec 21 - Dec 22
Comfort Inn & Suites Brattleboro I-91
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, (963)
"The room was perfect, and the food was great "
United States
Paul
The price is NT$3,675
NT$3,987 total
includes taxes & fees
Dec 18 - Dec 19
Keene Elm City Hotel, an Ascend Collection Hotel
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, (805)
"so clean and friendly it was a perfect stay!"
United States
Colette
The price is NT$4,489
NT$4,938 total
includes taxes & fees
Dec 22 - Dec 23
Best Western Springfield Hotel
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, (353)
"Clean comfy nice staff "
United States
Katherine
The price is NT$4,592
NT$4,982 total
includes taxes & fees
Dec 24 - Dec 25
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, (926)
"The room was very clean, and both staff and service were outstanding."
United States
Wonji
The price is NT$4,467
NT$4,914 total
includes taxes & fees
Dec 22 - Dec 23
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, (1002)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is NT$4,046
NT$4,390 total
includes taxes & fees
Dec 21 - Dec 22
Best Western Plus Keene Hotel
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers
On The River Inn

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1002)
"This place was charming!! Enjoyed everything about it and so much to do right there in the inn."
United States
Ross
The price is NT$6,020
NT$7,766 total
includes taxes & fees
Dec 22 - Dec 23
On The River 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, (3)
The price is NT$5,011
NT$5,512 total
includes taxes & fees
Jan 13 - 2026/1/14
Hideaway Inn Mt. Snow
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, (1001)
"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 NT$4,492
NT$4,941 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn Express Hotel & Suites Brattleboro by IHG
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

On The River Inn

On The River Inn

10/10 Excellent
"Clean rooms, front desk personal could use people skill update, not young lady there this am, she was great. Guys in restaurant were the best. "
Michael 2-night trip
Posted 2 days ago
On The River Inn

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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. The Shire Woodstock: Provides 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 center. Kimpton Taconic Hotel by IHG: Offers a full-service spa, an indoor pool, and free self parking. Pointe at Castle Hill Resort: Features buffet, an indoor pool, and complimentary wired internet access.
What is there to see and do in Chester?
Explore places like Stratton Mountain Resort while you're in the area. Make a point to visit attractions like DaVallia Art & Accents and Bonnie's Bundles Dolls. 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.