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

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Check availability on Chester Hotels with Pool

Tonight
20 Oct - 21 Oct
Tomorrow
21 Oct - 22 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Chester hotels with a pool

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 sofa, a coffee table, a desk, and a TV.
A hotel room with a bed, a sitting area, a bathroom with a bathtub, and a large mirror.

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.
3.939.345 ₫
4.333.280 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Best Western Springfield Hotel
An indoor swimming pool with four chairs and a hot tub.
A spa named Castle Hill Spa with a well-maintained lawn and a pathway leading to the entrance.
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.

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.
3.946.351 ₫
4.498.841 ₫ total
includes taxes & fees
28 Oct - 29 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 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".

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.
2.458.239 ₫
2.814.684 ₫ total
includes taxes & fees
19 Nov - 20 Nov
The Upper Pass 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 traditional bedroom with a four-poster bed, two armchairs, a wooden wardrobe, and a mirror.

4. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
6.969.152 ₫
7.596.375 ₫ total
includes taxes & fees
21 Oct - 22 Oct
Castle Hill Resort And Spa
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 hotel with multiple buildings, a covered outdoor area, and a snowy landscape.
A golf course with rolling hills, trees, and a distant mountain range.

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.
4.782.993 ₫
5.811.107 ₫ total
includes taxes & fees
18 Nov - 19 Nov
Jackson Gore Village, A Vail Resorts Property
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.

6. The Landgrove

The Landgrove
Londonderry
4.930.979 ₫
5.374.871 ₫ total
includes taxes & fees
25 Oct - 26 Oct
The Landgrove
A modern house with a pool, surrounded by lush greenery and mountains in the background.
A snow-covered cabin with a large window, surrounded by trees and a mountain 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.

7. 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.
3.858.802 ₫
4.244.682 ₫ total
includes taxes & fees
3 Nov - 4 Nov
Blue Gentian Lodge at Magic Mountain
A swimming pool with a clear blue water, surrounded by lounge chairs and a lifebuoy on the wall.
A spacious lobby with a reception desk, seating area, and a modern ceiling light fixture.
A hotel entrance with a modern design, featuring a prominent entrance canopy and stone pillars.
A hotel room with two beds, a microwave, a coffee maker, and a small kitchenette.

8. 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.
3.832.904 ₫
4.216.194 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Express Hotel & Suites Brattleboro by IHG
An indoor swimming pool with a tiled deck, safety signs, and a few chairs.
A hotel room with a bed, a sofa, a desk, and a chair. There are three framed pictures on the wall.
A hotel lobby with a reception desk, seating area, and a wall with framed pictures.
A hotel lobby with a reception desk, two sofas, a coffee station, and a dining area.

9. 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.
2.896.950 ₫
3.186.645 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Comfort Inn & Suites Brattleboro I-91
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 living room with a fireplace, a sofa, a coffee table, and a view through a sliding glass door.
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.
2.622.172 ₫
2.884.389 ₫ total
includes taxes & fees
3 Nov - 4 Nov
The Manchester View
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

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

8/10 Good
"The hotel was clean but older. Nothing special. Basic hotel room."
Shannon 2-night trip
Posted 11 hours ago
Pointe at Castle Hill Resort
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

10/10 Excellent
"The hotel was built in the 1990’s per the concierge, which surprised us, as it is so well maintained that it seems much newer! We booked a king bed room with (small) balcony. Our only complaint would be the bathroom toilet situation. Toilet is very small and way too close to the door…a very awkward setup, especially trying to get into the shower. The tub and shower however seemed completely new. Very nice! The room is quite large and the bed was very comfortable. I’m only 4’10” so it was a high hurdle for me, so I made up the couch bed and slept there. I usually bring a small folding stool but forgot it, so the couch bed was a nice option…it seems to be new and was comfortable. The first night we ate at the hotel restaurant and everything was very tasty, especially the Brussel sprouts and salmon. We were celebrating my husband’s birthday weekend, and brought wine but had to drink from coffee mugs as the hotel is “green” so no cups in the room. We snagged a couple cups from the restaurant for our second night. 😊 Also there’s no mini fridge. We had breakfast twice at 1MTN restaurant, which we highly recommend! Second night we had dinner at “Ten Tables”…their Berkshire Pork Chop was PHENOMENAL. 3rd night we drove down to Wilmington to “The Anchor”…every single thing was delicious! We had a superb weekend!"
Curtis 3-night trip
Posted 19 hours ago
Grand Summit Resort, A Vail Resorts Property
Colonial Motel

Colonial Motel

8/10 Good
"The rooms are quite large. There were a lot of unfinished projects going on, so the property was messy and slightly unkempt. The breakfast was terrible. Trash bags were left out attracting skunks. Price made it a 4 star."
Andrea 3-night trip
Posted 21 hours ago
Colonial Motel
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Beautiful resort with amazing beds! Very comfortable."
Sara 4-night trip
Posted 2 days ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

10/10 Excellent
"Good"
Kenton 2-night trip
Posted 7 days ago
The Equinox Golf Resort And Spa

Frequently asked questions

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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