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

Chester Hotel with Pool

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Check availability on Chester Hotel with Pool

Tonight
26 Sept - 27 Sept
Tomorrow
27 Sept - 28 Sept
Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct

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 kitchen with a coffee maker, mugs, and containers labeled 'Sugar' and 'Coffee'.

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.
HK$1,271
HK$3,374 total
includes taxes & fees
29 Sept - 30 Sept
Historic 150-year-old farmhouse, Jacuzzi included
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 Christmas tree decorated with lights, ornaments, and a bow.
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.

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.
HK$705
HK$807 total
includes taxes & fees
27 Sept - 28 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 sitting area, a bathroom with a bathtub, and a large mirror.
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 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.
HK$1,405
HK$1,545 total
includes taxes & fees
22 Oct - 23 Oct
Best Western Springfield Hotel
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 sign for Castle Hill Spa surrounded by lush greenery and a well-maintained lawn.

4. 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.
HK$1,325
HK$1,511 total
includes taxes & fees
18 Oct - 19 Oct
Pointe at Castle Hill Resort
A hotel with a swimming pool area, including two hot tubs and lounge chairs.
A multi-story building with a stone patio, outdoor seating, and a fire pit.
A couple standing on a balcony with a view of a hotel courtyard.
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.
HK$1,296
HK$1,575 total
includes taxes & fees
30 Sept - 1 Oct
Jackson Gore Village, A Vail Resorts Property
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.

6. 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.
HK$1,404
HK$1,544 total
includes taxes & fees
25 Oct - 26 Oct
Blue Gentian Lodge at Magic Mountain
A large stone building with a steep roof, surrounded by dense forest and hills.
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 spacious living room with a fireplace, comfortable seating, and a large window providing natural light.
A spacious living room with a fireplace, red sofas, a wooden coffee table, and a television.

7. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
HK$2,111
HK$2,301 total
includes taxes & fees
27 Sept - 28 Sept
Castle Hill Resort And Spa
A rectangular swimming pool with a metal ladder, surrounded by a white fence, and shaded by trees.
A spacious room with high ceilings, wooden beams, large windows, and tables and chairs arranged for dining.
A large two-story house with a front porch and a well-maintained lawn.
An aerial view of a residential area with houses, a tennis court, and a swimming pool.

8. The Landgrove

The Landgrove
Londonderry
HK$1,735
HK$1,891 total
includes taxes & fees
4 Oct - 5 Oct
The Landgrove
A swimming pool with a brick border and metal handrails.
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.
A room with a stone fireplace, large windows with curtains, a patterned rug, and a plush chair.

9. Windham Hill Inn

Windham Hill Inn
West Townshend
  • Serene seasonal outdoor pool offers 24-hour summer swimming amid Vermont's lush Windham Hills.
HK$1,458
HK$1,589 total
includes taxes & fees
20 Oct - 21 Oct
Windham Hill Inn
A bedroom with a fireplace, two beds, a chair, and a nightstand.
A wooden deck with two chairs and a table, surrounded by a wooden railing, overlooking a grassy area with trees and a distant road.
A green building with a wooden deck, a small porch, and a sign that reads 'Motel.'
A large, two-story house with a central entrance, surrounded by trees and a mountain backdrop.

10. The Manchester View

The Manchester View
Manchester Center
  • Mountain views from the pool create a picturesque escape at this serene Manchester retreat.
HK$842
HK$926 total
includes taxes & fees
26 Oct - 27 Oct
The Manchester View
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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
"Property has been renovated-it is very clean and modern. Nice simple breakfast served. Housekeeping didn’t show the 2nd day of our stay. ( we hunted them down for towels before getting ready for a wedding. They offered to come then- but it was too late in the day) Great views and quite location."
Cynthia 2-night trip
Posted 22 hours ago
The Manchester View
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent
"Nice hot tubs"
David 3-night trip
Posted 2 days ago
Jackson Gore Village, A Vail Resorts Property
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 3 days ago
The Equinox Golf Resort And Spa
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Very nice stay and nice rooms."
Nicole 1-night trip
Posted 4 days ago
Pointe at Castle Hill Resort
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 6 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 8 days ago
On The River Inn

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 such as Bonnie's Bundles Dolls and DaVallia Art & Accents. 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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