A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

Hotels with Swimming Pools in Chester

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Check availability on Chester Hotels with Swimming Pools

Our top choices for Chester hotels with a pool

Indoor pool

Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (868 reviews)
  • cleanliness
    Splash into mountain views at this hotel's warm indoor pool, perfect for year-round aquatic bliss.
The price is S$254
includes taxes & fees
23 Aug - 24 Aug
Best Western Springfield Hotel
Indoor pool

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
3.5 star property
Cavendish
8.8 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Dive into alpine luxury with this heated indoor pool and hot tub sanctuary, steps away from Okemo Mountain's world-class skiing.
The price is S$199
includes taxes & fees
19 Aug - 20 Aug
Pointe at Castle Hill Resort
Outdoor pool

The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
2.5 star property
Londonderry
8.2 out of 10, Very good, (701 reviews)
  • cleanliness
    Slope-side sanctuary beckons with mountain vistas and a seasonal outdoor pool.
The price is S$161
includes taxes & fees
23 Aug - 24 Aug
The Upper Pass Lodge at Magic Mountain
Seasonal outdoor pool

Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (120 reviews)
  • cleanliness
    Swim in the sunlit mountain waters at this alpine retreat's seasonal outdoor pool nestled in picturesque Vermont.
The price is S$210
includes taxes & fees
18 Aug - 19 Aug
Blue Gentian Lodge at Magic Mountain
Seasonal outdoor pool

The Landgrove

The Landgrove
3.5 star property
Londonderry
10.0 out of 10, Exceptional, (1 review)
The price is S$268
includes taxes & fees
24 Jul - 25 Jul
The Landgrove
Outdoor spa tub

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
3.0 star property
Jackson Gore Base Area
8.6 out of 10, Excellent, (873 reviews)
  • cleanliness
    Dive into pool perfection at this mountain resort with year-round swimming and spa relaxation.
The price is S$299
includes taxes & fees
23 Aug - 24 Aug
Jackson Gore Village, A Vail Resorts Property
Front of property

Castle Hill Resort And Spa

Castle Hill Resort And Spa
3.5 star property
Cavendish
9.0 out of 10, Wonderful, (120 reviews)
The price is S$326
includes taxes & fees
19 Aug - 20 Aug
Castle Hill Resort And Spa
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
3.0 star property
West Dover
8.6 out of 10, Excellent, (121 reviews)
The price is S$125
includes taxes & fees
10 Aug - 11 Aug
Hideaway Inn Mt. Snow
Indoor pool

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (1,000 reviews)
  • cleanliness
    Immerse in rejuvenating waters at this mountain-adjacent hotel featuring a pristine indoor pool and relaxing hot tub sanctuary.
The price is S$174
includes taxes & fees
3 Aug - 4 Aug
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
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Splash into family fun with a year-round indoor pool perfect for kids at this rural Vermont retreat.
The price is S$216
includes taxes & fees
5 Aug - 6 Aug
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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Choose what matters most at hotels with a pool in Chester

Breakfast included
4 stars

Top Chester Hotel Reviews

The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent
"Loved this little motel style resort. Our king room was HUGE. The water in the shower was HOT. AC wasn’t the best but kept us cool enough plus a fan above the bed. Stunning area and the small town near by is soo cute"
Lisa Or Mike 1-night trip
Posted 7 hours ago
The Palmer House Resort, an Ascend Collection Hotel

Frequently asked questions

What are some hotels with pools in Chester?
Fullerton Inn: Provides a seasonal outdoor pool, an indoor pool and 4 restaurants. Woodstock Inn & Resort: Features buffet, an indoor pool and complimentary high-speed (wired) Internet access. Keene Elm City Hotel, an Ascend Collection Hotel: Hotel, 1-minute walk from Green Mountain National Forest. Offers complimentary bicycles, a seasonal outdoor pool and a 24-hour fitness centre. Kimpton Taconic Hotel by IHG: Features buffet, an indoor pool and free self parking. Best Western Plus Keene Hotel: Offers a children's pool, an indoor pool and a sauna.
What is there to see and do in Chester?
Make a point to visit attractions such as DaVallia Art & Accents and Bonnie's Bundles Dolls. During your stay, visit sights such as Vermont Country Store, Lowell Lake State Park and Magic Mountain Ski Resort. 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.

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