Find Hotels with a Pool in Chester, VT

Start date: Check-in selected.
To Date
End date: Check-out

  • 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 Chester Hotels with a Pool

Tonight
3 Dec - 4 Dec
Tomorrow
4 Dec - 5 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Chester Hotels with a Pool

Exterior
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 SAR 524
SAR 1,612 total
includes taxes & fees
9 Dec - 10 Dec
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

2.0 star property
West Dover
10.0 out of 10, Exceptional, (1)
"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 SAR 480
SAR 528 total
includes taxes & fees
5 Dec - 6 Dec
Hideaway Inn Mt. Snow
Indoor pool, sun loungers
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 star property
Brattleboro
8.6 out of 10, Excellent, (736)
"Staff was friendly and pool was nice"
United States
Joshua
The price is SAR 432
SAR 476 total
includes taxes & fees
18 Dec - 19 Dec
Comfort Inn & Suites Brattleboro I-91
Indoor pool
Best Western Springfield Hotel

Best Western Springfield Hotel

2.5 star property
Springfield
8.8 out of 10, Excellent, (802)
"so clean and friendly it was a perfect stay!"
United States
Colette
The price is SAR 537
SAR 591 total
includes taxes & fees
16 Dec - 17 Dec
Best Western Springfield Hotel
Indoor pool
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, (957)
"Enjoyed the breakfast options and the very comfortable bed. "
Canada
Nancy
The price is SAR 409
SAR 443 total
includes taxes & fees
24 Dec - 25 Dec
Keene Elm City Hotel, an Ascend Collection Hotel
Indoor pool, open 6:00 AM to 10:00 PM, sun loungers
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3.0 star property
Keene
8.4 out of 10, Very Good, (1000)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is SAR 522
SAR 566 total
includes taxes & fees
11 Dec - 12 Dec
Best Western Plus Keene Hotel
Indoor pool
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

2.5 star property
Keene
8.8 out of 10, Excellent, (351)
"Nice place to stay, nice area, will stay again."
United States
Catherine
The price is SAR 552
SAR 599 total
includes taxes & fees
23 Dec - 24 Dec
Hampton Inn & Suites Keene
Indoor pool
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

3.0 star property
Keene
8.8 out of 10, Excellent, (1001)
"Lovely hotel"
United States
ronald
The price is SAR 603
SAR 654 total
includes taxes & fees
12 Dec - 13 Dec
Courtyard by Marriott Keene Downtown
Indoor pool
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 star property
Brattleboro
8.2 out of 10, Very Good, (924)
"The room was very clean, and both staff and service were outstanding."
United States
Wonji
The price is SAR 537
SAR 591 total
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn Brattleboro
Indoor pool
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, (1005)
"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 SAR 538
SAR 591 total
includes taxes & fees
7 Dec - 8 Dec
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.
View all properties

Top Chester Hotel Reviews

The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent
"Staff was courteous. The room was clean. "
Patricia 1-night trip
Posted 3 days ago
The Palmer House Resort, an Ascend Collection Hotel

Explore a world of travel with Expedia

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 complimentary bicycles, a seasonal outdoor pool, and a 24-hour fitness center. Kimpton Taconic Hotel by IHG: Features a seasonal outdoor pool, an indoor pool, and 4 restaurants. The Equinox Golf Resort & Spa: Offers buffet, an indoor pool, and complimentary wired internet access. Hampton Inn and Suites Manchester: Offers complimentary wired internet access, an indoor pool, and free self parking.
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.