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

Tonight
6 Oct - 7 Oct
Tomorrow
7 Oct - 8 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Chester hotels with a pool

An indoor swimming pool with four chairs and a hot tub.
A kitchen with wooden cabinets, a white microwave, a stove, and a refrigerator.
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.

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.
S$215
includes taxes & fees
21 Oct - 22 Oct
Pointe at Castle Hill Resort
An indoor swimming pool with clear water, lounge chairs, and a stone fireplace.
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.
A spacious, well-lit kitchen area with modern appliances, a central island with bar stools, and a chandelier.

2. 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.
S$214
includes taxes & fees
1 Nov - 2 Nov
Best Western Springfield Hotel
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 multi-story building with a stone patio, outdoor seating, and a fire pit.
A hotel with multiple buildings, a covered outdoor area, and a snowy landscape.

3. 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.
S$280
includes taxes & fees
26 Oct - 27 Oct
Jackson Gore Village, A Vail Resorts Property
A swimming pool with a wooden deck and a red building in the background.
A living room with a fireplace, a sofa, a coffee table, and a dining area with chairs and a table.
A bar area with a sign reading "MAGIC" and "featured Vermont beers".
A Christmas tree decorated with lights, ornaments, and a bow.

4. 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.
S$159
includes taxes & fees
1 Nov - 2 Nov
The Upper Pass Lodge at Magic Mountain
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 house with a balcony and a garden with red flowers.
A sunroom with a round table covered by a plaid tablecloth, surrounded by chairs, large windows offering a view of a garden and pond.

5. 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.
S$209
includes taxes & fees
5 Nov - 6 Nov
Blue Gentian Lodge at Magic Mountain
A bedroom with a fireplace, two beds, a chair, and a nightstand.
A green building with a wooden deck, a small porch, and a sign that reads 'Motel.'
A living room with a fireplace, a sofa, a coffee table, and a view through a sliding glass door.
A wooden deck with two chairs and a table, surrounded by a wooden railing, overlooking a grassy area with trees and a distant road.

6. The Manchester View

The Manchester View
Manchester Center
  • Mountain views from the pool create a picturesque escape at this serene Manchester retreat.
S$119
includes taxes & fees
5 Nov - 6 Nov
The Manchester View
A large stone building with a steep roof, surrounded by dense forest and hills.
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.
A traditional bedroom with a four-poster bed, two armchairs, a wooden wardrobe, and a mirror.

7. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
S$307
includes taxes & fees
19 Oct - 20 Oct
Castle Hill Resort And Spa
A rectangular swimming pool with a metal ladder, surrounded by a white fence, and shaded by trees.
A large two-story house with a front porch and a well-maintained lawn.
A spacious room with high ceilings, wooden beams, large windows, and tables and chairs arranged for dining.
A cozy interior with a bar area, wooden furniture, and a Christmas tree.

8. The Landgrove

The Landgrove
Londonderry
S$267
includes taxes & fees
13 Oct - 14 Oct
The Landgrove
A large indoor swimming pool with clear blue tiles, sunlit by large windows, and equipped with lounge chairs and a ceiling fan.
Two Adirondack chairs by a river with a forested hillside in the background.
A spacious living room with a chandelier, multiple armchairs, a coffee table, and a rug.
A two-story house with a balcony, surrounded by lush greenery and a pond.

9. On The River Inn

On The River Inn
West Woodstock
  • Splash into bliss with an indoor pool, hot tub, and children's splash area amid scenic views.
S$258
includes taxes & fees
1 Nov - 2 Nov
On The River Inn
A swimming pool with a clear blue water, surrounded by green grass and tall trees.
A modern building with a glass facade, a brick exterior, and a metal roof.
A cozy indoor space with a chalkboard sign advertising free fire entertainment from 7pm to 9pm.
A garden with various flowers and a stream.

10. Toll Road Inn

Toll Road Inn
Manchester Center
  • Indulge in a refreshing mountain retreat at this Vermont inn with a seasonal outdoor pool and rejuvenating hot tub experience.
S$179
includes taxes & fees
5 Nov - 6 Nov
Toll Road Inn
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

Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Clean rooms, very friendly staff, noise AC"
Abdolkarim 1-night trip
Posted 9 hours ago
Woodstock Inn & Resort
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

10/10 Excellent
"1"
Kevin 2-night trip
Posted 10 hours ago
Grand Summit Resort, A Vail Resorts Property
On The River Inn

On The River Inn

10/10 Excellent
"Everyone was so friendly and the food at breakfast and dinner was excellent! Looking forward to coming back next year!"
Erinn 1-night trip
Posted 12 hours ago
On The River Inn
The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

8/10 Good
"Older property that needs updating. Beds were very comfortable."
Peter 1-night trip
Posted 12 hours ago
The Palmer House Resort, an Ascend Collection Hotel
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"Great place to stay"
Joseph 1-night trip
Posted 17 hours ago
The Black Bear Lodge at Stratton Mountain Resort
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"The staff were very nice, room was clean, and the breakfast was good. All made for an easy night as we traveled through Manchester."
Thomas 1-night trip
Posted 19 hours ago
Hampton Inn and Suites Manchester
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent
"By far, our favorite place to stay at as a family. The staff is always very friendly, courteous and kind, and the property is breathtaking. The views of the mountains and the foliage were absolutely stunning. The rooms are spacious and well taken care of. We especially enjoyed the hot tubs with the Mountain View."
Emily 1-night trip
Posted 1 day ago
Jackson Gore Village, A Vail Resorts Property
Colonial Motel

Colonial Motel

10/10 Excellent
"clean room"
Biplob 1-night trip
Posted 2 days ago
Colonial Motel
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Very nice place, quiet and easily accessible. Room was large with separate large bedroom with door. Large LR with fireplace, sofa & recliner and fully stocked kitchen."
Mary 2-night trip
Posted 4 days ago
Pointe at Castle Hill Resort

Frequently asked questions

What are some hotels with pools in Chester?
Fullerton Inn: Features a seasonal outdoor pool, an indoor pool and 4 restaurants. Stone Hearth Inn and Eatery: Hotel, 1-minute walk from Green Mountain National Forest. Provides free self parking, a seasonal outdoor pool and complimentary bicycles. Woodstock Inn & Resort: Hotel, 1-minute walk from Green Mountain National Forest. Features daily, a seasonal outdoor pool and free self parking. The Jackson: Features a full-service spa, an indoor pool and free self parking. Grand Summit Resort, A Vail Resorts Property: Provides 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 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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