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

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Check availability on Chester Hotels with Pool

Tonight
5 Sep - 6 Sep
Tomorrow
6 Sep - 7 Sep
Next weekend
11 Sep - 13 Sep
In two weeks
18 Sep - 20 Sep

Our top choices for Chester hotels with a pool

An indoor swimming pool with four chairs and a hot tub.
A spacious lobby with a fireplace, leather seating, and a chandelier.
A spa named Castle Hill Spa with a well-maintained lawn and a pathway leading to the entrance.
A kitchen with wooden cabinets, a white microwave, a stove, and a refrigerator.

1. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
Cavendish
  • Dive into alpine luxury with this heated indoor pool and hot tub sanctuary, steps away from Okemo Mountain's world-class skiing.
3.746.392 ₫
4.270.887 ₫ total
includes taxes & fees
6 Sept - 7 Sept
Pointe at Castle Hill Resort
A swimming pool with a wooden deck and a red building in the background.
A restaurant with wooden tables and chairs, a central table with a sign reading "The Red Slate Restaurant", and large windows with views of the outside.
A Christmas tree decorated with lights, ornaments, and a bow.
A bar area with a sign reading "MAGIC" and "featured Vermont beers".

2. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
Londonderry
  • Slope-side sanctuary beckons with mountain vistas and a seasonal outdoor pool.
2.387.885 ₫
2.650.553 ₫ total
includes taxes & fees
7 Sept - 8 Sept
The Upper Pass Lodge at Magic Mountain
An indoor swimming pool with clear water, lounge chairs, and a stone fireplace.
A hotel room with a bed, a sofa, a coffee table, a desk, and a TV.
A hotel with a covered entrance, stone facade, and a sign indicating it is part of the Best Western chain.
A hotel room with a bed, a sitting area, a bathroom with a bathtub, and a large mirror.

3. Best Western Springfield Hotel

Best Western Springfield Hotel
Springfield
  • Splash into mountain views at this hotel's warm indoor pool, perfect for year-round aquatic bliss.
4.201.749 ₫
4.621.925 ₫ total
includes taxes & fees
14 Sept - 15 Sept
Best Western Springfield Hotel
A modern house with a pool, surrounded by lush greenery and mountains in the background.
A hot tub on a covered porch with a view of autumn foliage.
A snow-covered cabin with a large window, surrounded by trees and a mountain in the background.
A sunroom with a round table covered by a plaid tablecloth, surrounded by chairs, large windows offering a view of a garden and pond.

4. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
Londonderry
  • Swim in the sunlit mountain waters at this alpine retreat's seasonal outdoor pool nestled in picturesque Vermont.
3.885.920 ₫
4.274.513 ₫ total
includes taxes & fees
8 Sept - 9 Sept
Blue Gentian Lodge at Magic Mountain
A hotel with a swimming pool area, including two hot tubs and lounge chairs.
A couple standing on a balcony with a view of a hotel courtyard.
A golf course with rolling hills, trees, and a distant mountain range.
A hotel with multiple buildings, a covered outdoor area, and a snowy landscape.

5. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
  • Dive into pool perfection at this mountain resort with year-round swimming and spa relaxation.
4.536.289 ₫
5.511.518 ₫ total
includes taxes & fees
30 Sept - 1 Oct
Jackson Gore Village, A Vail Resorts Property
An indoor swimming pool with clear blue water, a lifebuoy, and a few lounge chairs.
A hotel room with a bed, a desk, a chair, a wooden door, and a window.
A modern fitness center with cardio machines, weightlifting equipment, and a large mirror.
A modern bathroom with a glass-enclosed shower, a white toilet, and a towel rack with two towels.

6. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
  • Splash into comfort at this indoor pool oasis offering year-round aquatic escape in Keene.
3.679.395 ₫
3.992.144 ₫ total
includes taxes & fees
6 Sept - 7 Sept
Keene Elm City Hotel, an Ascend Collection Hotel
An indoor swimming pool with a tiled edge, surrounded by lounge chairs and a small table.
A spacious lobby with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A bar area with a high ceiling and stained glass windows, bar stools, and a checkered floor.
A gazebo with a white fence and a blue roof, surrounded by a well-maintained lawn, with a brick building in the background.

7. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
  • Splash into luxury at this hotel's sparkling indoor pool, complete with plush sun loungers and serene atmosphere.
3.885.920 ₫
4.216.354 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Best Western Plus Keene Hotel
A large stone building with a steep roof, surrounded by dense forest and hills.
A traditional bedroom with a four-poster bed, two armchairs, a wooden wardrobe, and a mirror.
A spacious living room with a fireplace, comfortable seating, and a large window providing natural light.
A hotel room with a bed, a nightstand, a lamp, a door, and a view into another room with a couch and a window.

8. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
5.965.409 ₫
6.502.296 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Castle Hill Resort And Spa
View all properties

Choose what matters most at hotels with a pool in Chester

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Chester Hotel Reviews

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"All around great stay. Thank you."
Christina 3-night trip
Posted 14 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel
The Manchester View

The Manchester View

10/10 Excellent
"This property checks all of the boxes. The views of surrounding mountains are among the best in the area. The rooms were recently updated and very comfortable. The location is just a small 1 mile drive to the village and great restaurants."
Scott 1-night trip
Posted 21 hours ago
The Manchester View
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

8/10 Good
"My room had candy on side table and needed to have phone cleaned. Older property has character but needs attention in rooms. Don't pay for valet parking basically the same as self parking. Upon check out they handed me the keys to get car. I think it was overpriced for what you get. Manchester is a cute town. Nothing in the room to make coffee and had to buy water no refrigerators as well"
Renata 1-night trip
Posted 2 days ago
Kimpton Taconic Hotel by IHG
Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Beautiful as is the town"
Kevin 1-night trip
Posted 2 days ago
Woodstock Inn & Resort

Frequently asked questions

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 Connecticut River State Park. 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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