The Best Hotels with a Pool in Chester, VT from AED 340 in 2026

Q: What are some hotels with pools in Chester?

Fullerton Inn : Provides a seasonal outdoor pool, an indoor pool, and 4 restaurants. Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area : Features buffet, an indoor pool, and complimentary wired internet access. Woodstock Inn & Resort : Resort, 3-minute walk from Mount Snow. Offers a full-service spa, an outdoor pool, and 2 hot tubs. Keene Elm City Hotel, an Ascend Collection Hotel : Features a children's pool, an indoor pool, and a sauna. Grand Summit Resort, A Vail Resorts Property : Offers buffet, an indoor pool, and free self parking.

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Our top choices for Chester hotels with a pool

Historic 150-year-old farmhouse, Jacuzzi included

Chester Depot

Historic farmhouse offers year-round aquatic enjoyment with well-maintained outdoor pool and hot tub.

AED 1,592 total

includes taxes & fees

7 Jul - 8 Jul

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

Hideaway Inn Mt. Snow

West Dover

AED 336 total

includes taxes & fees

7 Jul - 8 Jul

Keene Elm City Hotel, an Ascend Collection Hotel

Keene

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

AED 474 total

includes taxes & fees

6 Jul - 7 Jul

The Landgrove

Londonderry

AED 645 total

includes taxes & fees

7 Jul - 8 Jul

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.

AED 507 total

includes taxes & fees

8 Jul - 9 Jul

Hampton Inn Brattleboro

Brattleboro

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

AED 494 total

includes taxes & fees

19 Jul - 20 Jul

Comfort Inn & Suites Brattleboro I-91

Brattleboro

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

AED 515 total

includes taxes & fees

2 Aug - 3 Aug

Best Western Springfield Hotel

Springfield

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

AED 724 total

includes taxes & fees

16 Jul - 17 Jul

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Choose what matters most at hotels with a pool in Chester

Breakfast included

4 stars

Top Chester Hotel Reviews

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent

"Great staff, breakfast options were great, both days. Room was clean, very quiet. You can’t beat the location. If I could give it more stars I would."

Best Western Plus Keene Hotel

10/10 Excellent

"A perfect place for 30 members of our clan to gather as we attended wedding festivities 1/2 hour away at Cobb Hill over three days. The breakfast (complimentary) had tons of choices, the pool was fun, the snacks near the front desk were perfect and most of all, the staff was very kind. My daughter with her husband and three children were in a huge room!"

The Equinox Golf Resort & Spa

8/10 Good

"The resort looks tired. It needs a few repairs. The staff was friendly. We did not eat at the resort, but the next tiem we stay I would like to stay longer. I am not convinced that we received the benefits of the resort that we paid for on our resort fee. I attended a wonderful yoga class with Jasmine. I highly recommend the yoga, and the pool looked inviting, and I wish I had swum laps there. We will try it again, but I think the resort is overpriced given the quality of the amenities and its condition."

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

8/10 Good

"Need blackout curtains (very bright before 6am) Overall nice and spacious room Air conditiones at times smells musty - needs to be cleaned? Bummer about pool being closed and ac not -working on lower level amenities (heat wave) Very pleasant staff- daily check ins via text appreciated"

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Frequently asked questions

What are some hotels with pools in Chester?

Fullerton Inn: Provides a seasonal outdoor pool, an indoor pool, and 4 restaurants. Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area: Features buffet, an indoor pool, and complimentary wired internet access. Woodstock Inn & Resort: Resort, 3-minute walk from Mount Snow. Offers a full-service spa, an outdoor pool, and 2 hot tubs. Keene Elm City Hotel, an Ascend Collection Hotel: Features a children's pool, an indoor pool, and a sauna. Grand Summit Resort, A Vail Resorts Property: Offers buffet, 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, 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