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

Hotels with Swimming Pool in Chester, Vermont

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Check availability on Chester Hotels with Swimming Pool

Tonight
Oct 16 - Oct 17
Tomorrow
Oct 17 - Oct 18
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 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 spacious, well-lit kitchen area with modern appliances, a central island with bar stools, and a chandelier.

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.
P9,591
P10,550 total
includes taxes & fees
Nov 1 - Nov 2
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.

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.
P9,188
P10,474 total
includes taxes & fees
Oct 18 - Oct 19
Pointe at Castle Hill Resort
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 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.

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.
P5,879
P6,732 total
includes taxes & fees
Oct 19 - Oct 20
The Upper Pass Lodge at Magic Mountain
A swimming pool with a lifeguard chair, pool lift, and a seating area with chairs and tables.
A hotel with a covered entrance, a flagpole with an American flag, and a brick building with multiple windows.
A two-story building with a patio area featuring outdoor seating and a stone fire pit.
A spacious living area with a fireplace, comfortable seating, and a stone accent wall.

4. 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.
P9,568
P10,525 total
includes taxes & fees
Nov 10 - Nov 11
Hampton Inn and Suites Manchester
A swimming pool with a clear blue water, surrounded by lounge chairs and a lifebuoy on the wall.
A hotel entrance with a modern design, featuring a prominent entrance canopy and stone pillars.
A spacious lobby with a reception desk, seating area, and a modern ceiling light fixture.
A hotel room with two beds, a microwave, a coffee maker, and a small kitchenette.

5. 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.
P8,764
P9,641 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Hotel & Suites Brattleboro by IHG
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 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.
P12,225
P14,852 total
includes taxes & fees
Oct 26 - Oct 27
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, 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.
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
P16,968
P18,495 total
includes taxes & fees
Oct 19 - Oct 20
Castle Hill Resort And Spa
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 lobby with a reception desk, two sofas, a coffee station, and a dining area.
A hotel room with a sofa, a coffee table, a chair, a desk, and a lamp.

8. 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.
P6,978
P7,676 total
includes taxes & fees
Nov 15 - Nov 16
Comfort Inn & Suites Brattleboro I-91
A large indoor swimming pool with clear water, surrounded by tiled walls and a ceiling with recessed lighting.
A lobby with wooden paneling, a fireplace, and two green armchairs.
A spacious lobby with a stone wall, a reception desk, and a large window.
A compact hotel room with a kitchenette, a sofa, a small table, and a window with curtains.

9. Hampton Inn Brattleboro

Hampton Inn Brattleboro
Brattleboro
  • Immerse in rejuvenating waters at this mountain-adjacent hotel featuring a pristine indoor pool and relaxing hot tub sanctuary.
P7,021
P7,723 total
includes taxes & fees
Nov 15 - Nov 16
Hampton Inn Brattleboro
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.
A cozy interior with a bar area, wooden furniture, and a Christmas tree.

10. The Landgrove

The Landgrove
Londonderry
P10,627
P11,583 total
includes taxes & fees
Oct 26 - Oct 27
The Landgrove
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

Colonial Motel

Colonial Motel

10/10 Excellent
"Value for money. Clean and conveniently located. Friendly staff."
Swaraj 2-night trip
Posted 2 hours ago
Colonial Motel
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

8/10 Good
"Ij kii it"
Kevin 2-night trip
Posted 13 hours ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Very nice hotel! Recommend"
Vladimir 1-night trip
Posted 21 hours ago
Hampton Inn and Suites Manchester
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

8/10 Good
"We could hear or neighbors like they were in our room. Luckily they weren't loud all night."
Ed 1-night trip
Posted 2 days ago
Jackson Gore Village, A Vail Resorts Property
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"The indoor pool was great. They have lights hanging in the courtyard. The ambiance is really nice. The restaurant has amazing food, no need to leave the hotel. We enjoyed our stay very much."
Mandy 1-night trip
Posted 2 days ago
Best Western Plus Keene Hotel
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"My sister and I needed a very last minute place to stay after our VRBO rental was not what we thought. The ladies at the front desk were really nice and very help. The beds and pillows were very comfortable and the room was very clean. The only issue is the area, it’s a bit of a drive if you want to shop however, one minute up the road is Murdoch’s restaurant and they had delicious food. We ate there twice. Just make sure to make a reservation. All in all it was a nice stay and we definitely suggest staying there."
Stephanie 1-night trip
Posted 3 days ago
Pointe at Castle Hill Resort
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

10/10 Excellent
"Good"
Kenton 2-night trip
Posted 3 days ago
The Equinox Golf Resort And Spa
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 5 days ago
The Black Bear Lodge at Stratton Mountain Resort
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 10 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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