The Best Hotels with a Pool in Chester, VT from ₩131,045 in 2026

Q: What are some hotels with pools in Chester?

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

aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont

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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

₩167,788 total

includes taxes & fees

May 31 - Jun 1

Aspen At Manchester

Manchester Center

Seasonal pool adventures await with ski storage and free bicycles at this garden retreat.

₩239,018 total

includes taxes & fees

Jun 3 - Jun 4

Keene Elm City Hotel, an Ascend Collection Hotel

Keene

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

₩229,065 total

includes taxes & fees

Jun 1 - Jun 2

Hampton Inn Brattleboro

Brattleboro

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

₩210,094 total

includes taxes & fees

Jun 14 - Jun 15

Best Western Springfield Hotel

Springfield

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

₩282,179 total

includes taxes & fees

Jun 3 - Jun 4

Black Mountain Inn

Brattleboro

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

₩230,971 total

includes taxes & fees

May 28 - May 29

Indoor pool, open 6:00 AM to 10:00 PM, sun 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.

₩242,155 total

includes taxes & fees

Jun 10 - Jun 11

Comfort Inn & Suites Brattleboro I-91

Brattleboro

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

₩227,157 total

includes taxes & fees

Jun 7 - Jun 8

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Choose what matters most at hotels with a pool in Chester

Breakfast included

4 stars

Top Chester Hotel Reviews

Hampton Inn and Suites Manchester

10/10 Excellent

"Super clean and spacious rooms. Central to everything. Very nice and helpful staff."

Hampton Inn Brattleboro

8/10 Good

"This is the best option in the area and we are big fans of the Hilton family of hotels (we stay there exclusively when this is an option). Everything was as expected for a Hampton Inn, including the workout room, layout of the room, and amenities. Five stars for pillows, hot water, and lack of noise. It was really hard getting an early check in, much harder than one would expect given the occupancy. We did end up getting it in plenty of time, which we appreciated. (It seemed like there were challenges with staffing.) We enjoyed our stay and would stay there again."

Best Western Plus Keene Hotel

2/10 Terrible

"This place is a dump Pretty much a motel Looks and smells dirty The curtains in bathroom are filthy The tub is disgusting and black No pride in the upkeep of this property Dirty walls and carpets Exposed outlets Didn’t even clean our room I only stayed here because Hampton inn was sold out NEVERRR AGAIN I even left a day early because I refused to raid a shower there"

Frequently asked questions

What are some hotels with pools in Chester?

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

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, The Nature Museum, and Lowell Lake 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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