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

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Check availability on Chester Hotels with a Pool

Tonight
Sep 24 - Sep 25
Tomorrow
Sep 25 - Sep 26
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Chester hotels with a pool

A two-story house with a porch, a small garden, and a well-maintained lawn.
A kitchen with a wooden island, stainless steel appliances, and a view of the outdoors through a window.
A wooden staircase leading to a door with a wreath, a potted plant, and a framed picture on the wall.
A hot tub in a forested area with a grill and a sign.

1. Historic 150-year-old farmhouse, Jacuzzi included

Historic 150-year-old farmhouse, Jacuzzi included
Chester Depot
  • Historic farmhouse offers year-round aquatic enjoyment with well-maintained outdoor pool and hot tub.
￥26,352
￥73,122 total
includes taxes & fees
Sep 29 - Sep 30
Historic 150-year-old farmhouse, Jacuzzi included
An indoor swimming pool with four chairs and a hot tub.
A sign for Castle Hill Spa surrounded by lush greenery and a well-maintained lawn.
A kitchen with wooden cabinets, a white microwave, a stove, and a refrigerator.
A spacious lobby with a fireplace, leather seating, and a chandelier.

2. 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.
￥18,416
￥20,995 total
includes taxes & fees
Oct 25 - Oct 26
Pointe at Castle Hill Resort
An indoor swimming pool with clear water, lounge chairs, and a stone fireplace.
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.
A hotel room with a bed, a sofa, a coffee table, a desk, and a TV.

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.
￥28,201
￥31,021 total
includes taxes & fees
Oct 18 - Oct 19
Best Western Springfield Hotel
A swimming pool with a wooden deck and a red building in the background.
A bar area with a sign reading "MAGIC" and "featured Vermont beers".
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 living room with a fireplace, a sofa, a coffee table, and a dining area with chairs and a table.

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.
￥16,037
￥18,362 total
includes taxes & fees
Sep 28 - Sep 29
The Upper Pass Lodge at Magic Mountain
A modern house with a pool, surrounded by lush greenery and mountains in the background.
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.
A hot tub on a covered porch with a view of autumn foliage.

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.
￥28,330
￥31,163 total
includes taxes & fees
Oct 25 - Oct 26
Blue Gentian Lodge at Magic Mountain
A hotel with a swimming pool area, including two hot tubs and lounge chairs.
A hotel with multiple buildings, a covered outdoor area, and a snowy landscape.
A golf course with rolling hills, trees, and a distant mountain range.
A couple standing on a balcony with a view of a hotel courtyard.

6. 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.
￥26,154
￥31,777 total
includes taxes & fees
Sep 30 - Oct 1
Jackson Gore Village, A Vail Resorts Property
A large stone building with a steep roof, surrounded by dense forest and hills.
A spacious living room with a fireplace, red sofas, a wooden coffee table, and a television.
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.

7. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
￥34,935
￥38,079 total
includes taxes & fees
Oct 18 - Oct 19
Castle Hill Resort And Spa
A rectangular swimming pool with a metal ladder, surrounded by a white fence, and shaded by trees.
A cozy interior with a bar area, wooden furniture, and a Christmas tree.
A spacious room with high ceilings, wooden beams, large windows, and tables and chairs arranged for dining.
An aerial view of a residential area with houses, a tennis court, and a swimming pool.

8. The Landgrove

The Landgrove
Londonderry
￥34,430
￥37,529 total
includes taxes & fees
Sep 29 - Sep 30
The Landgrove
A swimming pool with a brick border and metal handrails.
A room with a stone fireplace, large windows with curtains, a patterned rug, and a plush chair.
A stone pathway leading to a porch with a wooden railing, surrounded by lush greenery and a lattice fence.
A large, white, two-story house with a steeply pitched roof, a balcony, and a staircase leading to the upper floor.

9. Windham Hill Inn

Windham Hill Inn
West Townshend
  • Serene seasonal outdoor pool offers 24-hour summer swimming amid Vermont's lush Windham Hills.
￥29,262
￥31,896 total
includes taxes & fees
Oct 20 - Oct 21
Windham Hill Inn
A rectangular swimming pool surrounded by a white picket fence, with lounge chairs and an umbrella on one side.
A modern living room with a wooden dining table, sofa, and fireplace.
A spacious room with wooden floors, large windows, and black yoga mats.
An outdoor dining setup with a view of mountains and trees.

10. Aspen At Manchester

Aspen At Manchester
Manchester Center
  • Seasonal pool adventures await with ski storage and free bicycles at this garden retreat.
￥15,797
￥19,116 total
includes taxes & fees
Oct 25 - Oct 26
Aspen At Manchester
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

The Manchester View

The Manchester View

10/10 Excellent
"Very cool unique setting and property. The bed was like a cloud and very relaxing."
David B 1-night trip
Posted 18 hours ago
The Manchester View
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

8/10 Good
"Lovely setting and cozy atmosphere. No coffee maker or mini fridge in room due to electrical system. Pool, hot tub, steam room and sauna were good. Needs to be managed a little better."
Nancy 3-night trip
Posted 1 day ago
The Equinox Golf Resort And Spa
Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Wonderful inn! Everything was wonderful: rooms, food, etc!!"
Ann 2-night trip
Posted 2 days ago
Woodstock Inn & Resort
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Very nice stay and nice rooms."
Nicole 1-night trip
Posted 2 days ago
Pointe at Castle Hill Resort
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Wonderful relaxing stay!"
Rosemary 2-night trip
Posted 2 days ago
Hampton Inn and Suites Manchester
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent
"Nice"
Thomas 3-night trip
Posted 3 days ago
Jackson Gore Village, A Vail Resorts Property
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

8/10 Good
"The pool was not available due to repair. The parking was limited (we had to walk up/down the hill to overflow parking). The faucet in our room made machine gun noise. The room was pretty big and clean. Deli was good. The restaurant bartender was very helpful. The shuttle bus service was great."
Hisayo 2-night trip
Posted 4 days ago
Grand Summit Resort, A Vail Resorts Property
On The River Inn

On The River Inn

8/10 Good
"Extremely quaint and love the rooms and balcony… Dining room gorgeous Wish there were Apps on the Tv for streaming… that’s all"
Marcia 2-night trip
Posted 6 days ago
On The River Inn
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Absolutely beautiful location. Everything was perfect."
Shannon 4-night trip
Posted 6 days ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

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. Features daily, a seasonal outdoor pool, and free self parking. Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area: Offers a full-service spa, an indoor pool, and free self parking. Woodstock Inn & Resort: Offers a children's pool, an indoor pool, and a sauna. The Jackson: Hotel, 1-minute walk from Green Mountain National Forest. Features a seasonal outdoor pool, an indoor pool, and 4 restaurants.
What is there to see and do in Chester?
Make a point to visit attractions like Bonnie's Bundles Dolls and DaVallia Art & Accents. During your stay, check out sights such as Vermont Country Store, Lowell Lake State Park, and Connecticut River State Park. 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.

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