🏊 Top 10 Chester Hotels with Swimming Pool

Q: What are some hotels with pools in Chester?

Fullerton Inn : Provides a seasonal outdoor pool, an indoor pool and 4 restaurants. Woodstock Inn & Resort : Features a full-service spa, an indoor pool and free self parking. Pointe at Castle Hill Resort : Offers complimentary bicycles, a seasonal outdoor pool and a 24-hour fitness centre. Kimpton Taconic Hotel by IHG : Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Hampton Inn Brattleboro : Provides a seasonal outdoor pool, an indoor pool and 4 restaurants.

Check availability on Chester Hotels with Swimming Pools

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Our top choices for Chester hotels with a pool

Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas

Hideaway Inn Mt. Snow

West Dover

RM441 total

includes taxes & fees

26 May - 27 May

Hampton Inn Brattleboro

Brattleboro

Immerse in rejuvenating waters at this mountain-adjacent hotel featuring a pristine indoor pool and relaxing hot tub sanctuary.

RM552 total

includes taxes & fees

7 Jun - 8 Jun

Best Western Springfield Hotel

Springfield

Splash into mountain views at this hotel's warm indoor pool, perfect for year-round aquatic bliss.

RM741 total

includes taxes & fees

2 Jun - 3 Jun

Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Splash into comfort at this indoor pool oasis offering year-round aquatic escape in Keene.

RM602 total

includes taxes & fees

28 May - 29 May

Indoor pool, open 6:00 AM to 10:00 PM, pool loungers

Best Western Plus Keene Hotel

Keene

Splash into luxury at this hotel's sparkling indoor pool, complete with plush sun loungers and serene atmosphere.

RM662 total

includes taxes & fees

25 May - 26 May

Comfort Inn & Suites Brattleboro I-91

Brattleboro

Relaxing indoor pool retreat with comfortable loungers sets the perfect stage for your Vermont ski getaway.

RM600 total

includes taxes & fees

28 May - 29 May

Indoor pool, open 8:00 AM to 10:00 PM, pool loungers

On The River Inn

West Woodstock

Splash into bliss with an indoor pool, hot tub, and children's splash area amid scenic views.

RM886 total

includes taxes & fees

26 May - 27 May

Black Mountain Inn

Brattleboro

Refreshing poolside retreat in Black Mountain with seasonal swimming and scenic garden views.

RM579 total

includes taxes & fees

25 May - 26 May

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Choose what matters most at hotels with a pool in Chester

Breakfast included

4 stars

Top Chester Hotel Reviews

Best Western Plus Keene Hotel

10/10 Excellent

"Bueno"

Woodstock Inn & Resort

10/10 Excellent

"The Woodstock Inn is simply one of the most gracious and inviting hotels my wife and I have ever stayed in. We recently decided to vacation in Vermont and finally see what the Inn was about. First, the setting and common areas are magnificent, with many areas to sit and relax. The reading room has chess and backgammon boards and dozens of books to read. It even has a wood-paneled game room with shuffleboard, pool, and yes even a vintage Ms. Pacman game! Our room was clean and well-appointed, with the most sumptuous King bed you could imagine. Elegant bath with subway tile and all new fixtures. Here's the bonus - the Inn's athletic facility is off-premise by a mile but it is a large facility with multiple work-out rooms, Olympic-size pool with hot tub, and daily classes. Fantastic! And finally, here is our favorite part - the collection of amiable doormen that really set the character of the Inn. Fun, engaging, and completely focused on service. Thank you Larry, Mark, and all of you for a wonderful stay! Hope to see you next year."

The Palmer House Resort, an Ascend Collection Hotel

6/10 Okay

"Comfy room and bed. Very clean. Pillows were too fat. There were roof shingles on the deck and the deck wood needs some sanding. The buildings where the suites are located needs serious roof work. Grounds are beautiful and well maintained. Staff was awesome!"

Frequently asked questions

What are some hotels with pools in Chester?

Fullerton Inn: Provides a seasonal outdoor pool, an indoor pool and 4 restaurants. Woodstock Inn & Resort: Features a full-service spa, an indoor pool and free self parking. Pointe at Castle Hill Resort: Offers complimentary bicycles, a seasonal outdoor pool and a 24-hour fitness centre. Kimpton Taconic Hotel by IHG: Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Hampton Inn Brattleboro: Provides 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 DaVallia Art & Accents and Bonnie's Bundles Dolls. During your stay, visit sights such as Vermont Country Store, Lowell Lake State Park and Magic Mountain Ski Resort. 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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Check availability on Chester Hotels with Swimming Pools

Our top choices for Chester hotels with a pool

Hideaway Inn Mt. Snow

Hampton Inn Brattleboro

Best Western Springfield Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

Best Western Plus Keene Hotel

Comfort Inn & Suites Brattleboro I-91

On The River Inn

Black Mountain Inn

Hampton Inn & Suites Keene

Choose what matters most at hotels with a pool in Chester

Top Chester Hotel Reviews

Best Western Plus Keene Hotel

The Equinox Golf Resort & Spa

Hampton Inn and Suites Manchester

Hampton Inn Brattleboro

Woodstock Inn & Resort

Keene Elm City Hotel, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

On The River Inn

Pointe at Castle Hill Resort

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