Hotels with Pool & Resorts in Chester from NZ$187

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Check availability on Chester Hotels with Pool

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

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 NZ$870
includes taxes & fees
7 Jan - 8 Jan 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 NZ$248
includes taxes & fees
5 Jan - 6 Jan 2026
Hideaway Inn Mt. Snow
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, (746)
"Spectular continental breakfast and really nice staff. Room was clean and beautiful. Amazing stay overall!"
United States
Jack
The price is NZ$226
includes taxes & fees
31 Dec - 1 Jan 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 NZ$287
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, (968)
"Staff was very welcoming and the room was very clean. "
United States
Rebecca
The price is NZ$231
includes taxes & fees
28 Dec - 29 Dec
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 NZ$277
includes taxes & fees
3 Jan - 4 Jan 2026
Hampton Inn Brattleboro
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 NZ$258
includes taxes & fees
1 Jan - 2 Jan 2026
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 NZ$271
includes taxes & fees
31 Dec - 1 Jan 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 NZ$308
includes taxes & fees
25 Jan - 26 Jan 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 NZ$187
includes taxes & fees
31 Dec - 1 Jan 2026
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

On The River Inn

On The River Inn

10/10 Excellent
"Nice experience. Great location, good property, excellent service and care taking"
Kapil Amitabh 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 centre. 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 high-speed (wired) Internet access.
What is there to see and do in Chester?
Explore places such as Okemo Mountain Resort and 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.