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
Dec 25 - Dec 26
Tomorrow
Dec 26 - Dec 27
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

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 ￥31,578
￥79,207 total
includes taxes & fees
Jan 7 - Jan 8, 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, (4)
"Really happy with our stay and the way we felt at this hideaway "
United States
Edwin
The price is ￥20,548
￥22,603 total
includes taxes & fees
Jan 5 - Jan 6, 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, (744)
"Spectular continental breakfast and really nice staff. Room was clean and beautiful. Amazing stay overall!"
United States
Jack
The price is ￥18,365
￥20,202 total
includes taxes & fees
Dec 28 - Dec 29
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 ￥23,720
￥26,093 total
includes taxes & fees
Jan 5 - Jan 6, 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 ￥18,370
￥19,932 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 ￥22,889
￥25,178 total
includes taxes & fees
Jan 3 - Jan 4, 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 ￥21,676
￥23,519 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, (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 ￥22,455
￥24,701 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, (358)
"Clean comfy nice staff "
United States
Katherine
The price is ￥25,680
￥27,862 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, (474)
"Clean, very friendly staff. Will stay again."
United States
Scot
The price is ￥15,439
￥16,983 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.
View all properties

Top Chester Hotel Reviews

On The River Inn

On The River Inn

10/10 Excellent
"Rearaurant staff was top notch. "
Daniel 1-night trip
Posted 4 days ago
On The River Inn

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.