Book the Best Hotels with POOL in Chester in 2026

Q: What are some hotels with pools in Chester?

Fullerton Inn : Offers a seasonal outdoor pool, an indoor pool, and 4 restaurants. Woodstock Inn & Resort : Provides buffet, an indoor pool, and complimentary wired internet access. Keene Elm City Hotel, an Ascend Collection Hotel : Offers buffet, an indoor pool, and free self parking. Grand Summit Resort, A Vail Resorts Property : Features a children's pool, an indoor pool, and a sauna. Best Western Plus Keene Hotel : Provides complimentary bicycles, a seasonal outdoor pool, and a 24-hour fitness center.

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

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Our top choices for Chester hotels with a pool

Keene Elm City Hotel, an Ascend Collection Hotel

Keene

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

CA $183 total

includes taxes & fees

Jul 13 - Jul 14

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

Hideaway Inn Mt. Snow

West Dover

CA $135 total

includes taxes & fees

Jul 22 - Jul 23

Hampton Inn Brattleboro

Brattleboro

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

CA $190 total

includes taxes & fees

Jul 19 - Jul 20

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.

CA $203 total

includes taxes & fees

Jul 26 - Jul 27

Best Western Springfield Hotel

Springfield

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

CA $279 total

includes taxes & fees

Jul 26 - Jul 27

The Landgrove

Londonderry

CA $307 total

includes taxes & fees

Jul 23 - Jul 24

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.

CA $202 total

includes taxes & fees

Jul 26 - Jul 27

The Upper Pass Lodge at Magic Mountain

Londonderry

Slope-side sanctuary beckons with mountain vistas and a seasonal outdoor pool.

CA $199 total

includes taxes & fees

Jul 19 - Jul 20

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Choose what matters most at hotels with a pool in Chester

Breakfast included

4 stars

Top Chester Hotel Reviews

Woodstock Inn & Resort

10/10 Excellent

"As always - best hotel in Vermont."

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent

"The room itself was terrific. It was spacious and quiet. The pools- both indoor and outdoor were closed. There are signs saying there will be new pools in 2008. The construction was not started yet, so I have no idea why they needed to be closed already. We still had to pay a $15/day resort fee even though we couldn’t use the pool."

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent

"They noticed i had a 13 year old daughter and 9 year old son in toe. The upgrade to a suíte was complimentary and close to the pool. Definitely suggest this place. Breakfast was good and everything is close. We really enjoyed our stay."

Frequently asked questions

What are some hotels with pools in Chester?

Fullerton Inn: Offers a seasonal outdoor pool, an indoor pool, and 4 restaurants. Woodstock Inn & Resort: Provides buffet, an indoor pool, and complimentary wired internet access. Keene Elm City Hotel, an Ascend Collection Hotel: Offers buffet, an indoor pool, and free self parking. Grand Summit Resort, A Vail Resorts Property: Features a children's pool, an indoor pool, and a sauna. Best Western Plus Keene Hotel: Provides complimentary bicycles, a seasonal outdoor pool, and a 24-hour fitness center.

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 Magic Mountain Ski Resort. 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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Our top choices for Chester hotels with a pool