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

Chester Hotel Guide - Hotels with Pool in Chester, Vermont

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Check availability on Chester Hotels with Pool

Tonight
11 Oct - 12 Oct
Tomorrow
12 Oct - 13 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

Our top choices for Chester hotels with a pool

A two-story house with a front porch, a garage, and a well-maintained lawn.
A kitchen with a coffee maker, mugs, and containers labeled 'Sugar' and 'Coffee'.
A hot tub in a forested area with a grill and a sign.
A wooden staircase leading to a door with a wreath, a potted plant, and a framed picture on the wall.

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.
€390
includes taxes & fees
1 Nov - 2 Nov
Historic 150-year-old farmhouse, Jacuzzi included
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.

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.
€146
includes taxes & fees
18 Oct - 19 Oct
Pointe at Castle Hill Resort
A swimming pool with a wooden deck and a red building in the background.
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.
A bar area with a sign reading "MAGIC" and "featured Vermont beers".

3. 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.
€99
includes taxes & fees
12 Oct - 13 Oct
The Upper Pass Lodge at Magic Mountain
An indoor swimming pool with clear water, lounge chairs, and a stone fireplace.
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.
A hotel with a covered entrance, stone facade, and a sign indicating it is part of the Best Western chain.

4. 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.
€149
includes taxes & fees
1 Nov - 2 Nov
Best Western Springfield Hotel
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 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.

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.
€146
includes taxes & fees
3 Nov - 4 Nov
Blue Gentian Lodge at Magic Mountain
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 cozy interior with a bar area, wooden furniture, and a Christmas tree.
An aerial view of a residential area with houses, a tennis court, and a swimming pool.

6. The Landgrove

The Landgrove
Londonderry
€196
includes taxes & fees
8 Nov - 9 Nov
The Landgrove
A hotel with a swimming pool area, including two hot tubs and lounge chairs.
A golf course with rolling hills, trees, and a distant mountain range.
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.

7. 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.
€200
includes taxes & fees
9 Nov - 10 Nov
Jackson Gore Village, A Vail Resorts Property
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 traditional bedroom with a four-poster bed, two armchairs, a wooden wardrobe, and a mirror.
A spacious living room with a fireplace, red sofas, a wooden coffee table, and a television.

8. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
€262
includes taxes & fees
19 Oct - 20 Oct
Castle Hill Resort And Spa
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.

9. The Manchester View

The Manchester View
Manchester Center
  • Mountain views from the pool create a picturesque escape at this serene Manchester retreat.
€99
includes taxes & fees
3 Nov - 4 Nov
The Manchester View
A swimming pool with a brick border and metal handrails.
A kitchen with wooden cabinets, a built-in stove, a microwave, and a sink.
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.

10. Windham Hill Inn

Windham Hill Inn
West Townshend
  • Serene seasonal outdoor pool offers 24-hour summer swimming amid Vermont's lush Windham Hills.
€172
includes taxes & fees
22 Oct - 23 Oct
Windham Hill 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
"Room was spacious and very clean upon arrival. Staff was also very attentive and took care all our needs."
Marlene 3-night trip
Posted less than an hour ago
Woodstock Inn & Resort
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

8/10 Good
"Room was adequate. Bedding was uncomfortable. We would not revisit this property. We would not recommend to others."
Bruce 4-night trip
Posted 3 hours ago
Pointe at Castle Hill Resort
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

8/10 Good
"Nice clean rooms comfortable, breakfast was a nice way to start today."
Alain 2-night trip
Posted 3 hours ago
The Black Bear Lodge at Stratton Mountain Resort
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Great location and staff is AWESOME! Thanks for another pleasant stay!!"
Carey 1-night trip
Posted 2 days ago
Hampton Inn and Suites Manchester
The Manchester View

The Manchester View

10/10 Excellent
"We loved this property, our view opened up to magnificent Mountain View, if you are there during lead peeping season you know that makes a difference. We enjoyed the hot tub at night and the fireplace . Kind staff, they left cookies and bowls for our dog, breakfast was delicious, the variety of baked goods was perfect and the Vermont coffee provided brought up to a higher level I can’t wait to go back for a longer stay"
Cathya 1-night trip
Posted 2 days ago
The Manchester View
Colonial Motel

Colonial Motel

8/10 Good
"very convenient and cost was good, as we stay in Brattleboro as our daughter and granddaughter live in Turners Falls Mass. and its only a half hour drive to visit with them."
Leonard 3-night trip
Posted 3 days ago
Colonial Motel
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

8/10 Good
"Allen in the restaurant is great."
Bettina 1-night trip
Posted 5 days ago
Grand Summit Resort, A Vail Resorts Property
On The River Inn

On The River Inn

10/10 Excellent
"Karen at the front desk was absolutely delightful. She saw me struggling with my dog and bags, and helped me to my room. Dan on the housekeeping was so nice. We saw him almost every day. The hotel is incredibly pet friendly. It's so convenient to walk out of your room directly onto the rear lawn, and down toward the river. I had a nice chat with the lady who lives across the river. She also has a dog. The drive to downtown was just a few minutes. I highly recommend the farmer's market (you pass it on the way to downtown Woodstock). The room was very clean. The sink and bathroom door could use some updates, but other than that it was lovely. I would definitely return again with my pup."
VS 4-night trip
Posted 5 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. Provides free self parking, a seasonal outdoor pool and complimentary bicycles. Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area: Hotel, 1-minute walk from Green Mountain National Forest. Features daily, a seasonal outdoor pool and free self parking. Woodstock Inn & Resort: Features a full-service spa, an indoor pool and free self parking. The Jackson: 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.