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
Oct 12 - Oct 13
Tomorrow
Oct 13 - Oct 14
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Chester hotels with a pool

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.

1. 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.
₩203,867
₩224,254 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Springfield Hotel
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 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.

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.
₩192,741
₩219,725 total
includes taxes & fees
Oct 18 - Oct 19
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.

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.
₩247,519
₩300,728 total
includes taxes & fees
Nov 10 - Nov 11
Jackson Gore Village, A Vail Resorts Property
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 bar area with a sign reading "MAGIC" and "featured Vermont beers".
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.
₩128,344
₩146,953 total
includes taxes & fees
Oct 15 - Oct 16
The Upper Pass Lodge at Magic Mountain
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 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.

5. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
₩360,664
₩393,124 total
includes taxes & fees
Oct 19 - Oct 20
Castle Hill Resort And Spa
A swimming pool with a lifeguard chair, pool lift, and a seating area with chairs and tables.
A spacious living area with a fireplace, comfortable seating, and a stone accent wall.
A treats display with snacks and sundries.
A hotel with a covered entrance, a flagpole with an American flag, and a brick building with multiple windows.

6. Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester
Manchester Center
  • Rejuvenating indoor pool sanctuary with mountain views offers a tranquil retreat after a day on the nearby ski slopes.
₩203,921
₩224,313 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn and Suites Manchester
A swimming pool with a clear blue water, surrounded by lounge chairs and a lifebuoy on the wall.
A spacious lobby with a large flat-screen TV, modern seating, and a large window with a cityscape view.
A hotel room with two beds, a microwave, a coffee maker, and a small kitchenette.
A spacious lobby with a reception desk, seating area, and a modern ceiling light fixture.

7. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
Brattleboro
  • Splash into family fun with a year-round indoor pool perfect for kids at this rural Vermont retreat.
₩198,358
₩218,194 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Express Hotel & Suites Brattleboro by IHG
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 sunroom with a round table covered by a plaid tablecloth, surrounded by chairs, large windows offering a view of a garden and pond.
A house with a balcony and a garden with red flowers.

8. 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.
₩199,699
₩219,669 total
includes taxes & fees
Nov 3 - Nov 4
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.

9. The Manchester View

The Manchester View
Manchester Center
  • Mountain views from the pool create a picturesque escape at this serene Manchester retreat.
₩135,701
₩149,271 total
includes taxes & fees
Nov 3 - Nov 4
The Manchester View
An indoor swimming pool with a tiled deck, safety signs, and a few chairs.
A hotel lobby with a reception desk, seating area, and a wall with framed pictures.
A hotel room with a sofa, a coffee table, a chair, a desk, and a lamp.
A hotel room with a bed, a sofa, a desk, and a chair. There are three framed pictures on the wall.

10. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
  • Relaxing indoor pool retreat with comfortable loungers sets the perfect stage for your Vermont ski getaway.
₩148,273
₩163,101 total
includes taxes & fees
Nov 8 - Nov 9
Comfort Inn & Suites Brattleboro I-91
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

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

8/10 Good
""Great location, and the staff made it right!" The room was on the smaller side, and we had an issue with the AC. The staff quickly gave us a new room and handled our luggage, so we didn't have to move it ourselves. We slept peacefully after that. The location is great, and there are plenty of options nearby for kids to play. We will definitely book again!"
Bharath Reddy 1-night trip
Posted 1 hour ago
Jackson Gore Village, A Vail Resorts Property
The Manchester View

The Manchester View

8/10 Good
"Beautiful room, very clean and new. It was very bare in the room though. Breakfast from 8-10 and we went at 9:40, it was wiped out with nobody refilling so make sure you go early. Next day we went early and it was delicious! Hot tub was amazing which we used both nights. Overall, the views are gorgeous and highly recommend this hotel."
Marybeth 2-night trip
Posted 2 hours ago
The Manchester View
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Very clean and nice hotel with comfortable beds! Appreciated the bar/ restaurant right next door!"
Rhonda 1-night trip
Posted 3 hours ago
Hampton Inn and Suites Manchester
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

8/10 Good
"The hotel needs some updating, and could be a little cleaner. Bathroom door looked like it had not been cleaned in a long time. The staff was friendly, and breakfast was good."
Teresa D 1-night trip
Posted 22 hours ago
Best Western Plus Keene Hotel
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 1 day ago
Woodstock Inn & Resort
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"It's a great place to stay! I've been there several times in different seasons. Off-season or leaf peeper season the free breakfast is a lot less than the free breakfast during ski season. During ski season AKA winter, eggs, waffles, pancakes etc however during other seasons they only offer cold cereal, milk bagels toast and juice and coffee of course. Other than that it's a fantastic place and they're dog friendly"
Bridget 1-night trip
Posted 1 day ago
The Black Bear Lodge at Stratton Mountain Resort
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 4 days ago
Colonial Motel
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 6 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. 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 like DaVallia Art & Accents and Bonnie's Bundles Dolls. 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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