TOP Hotels with Pool in Chester, VT for 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 high-speed (wired) Internet access. Keene Elm City Hotel, an Ascend Collection Hotel : Hotel, 1-minute walk from Green Mountain National Forest. Features complimentary bicycles, a seasonal outdoor pool and a 24-hour fitness centre. Kimpton Taconic Hotel by IHG : 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.

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

1. Best Western Springfield Hotel

Springfield

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

฿6,588 total

includes taxes & fees

17 Aug - 18 Aug

2. 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.

฿6,442 total

includes taxes & fees

10 Aug - 11 Aug

3. Castle Hill Resort And Spa

Cavendish

฿9,807 total

includes taxes & fees

6 Aug - 7 Aug

4. 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.

฿5,700 total

includes taxes & fees

17 Aug - 18 Aug

5. 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.

฿6,363 total

includes taxes & fees

9 Aug - 10 Aug

6. Comfort Inn & Suites Brattleboro I-91

Brattleboro

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

฿4,761 total

includes taxes & fees

31 Aug - 1 Sept

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

7. Best Western Plus Keene Hotel

Keene

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

฿5,406 total

includes taxes & fees

4 Aug - 5 Aug

8. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

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

฿4,281 total

includes taxes & fees

1 Sept - 2 Sept

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Choose what matters most at hotels with a pool in Chester

Breakfast included

4 stars

Top Chester Hotel Reviews

Grand Summit Resort, A Vail Resorts Property

10/10 Excellent

"Very nice resort, on a beautiful landscaping"

Colonial Motel

8/10 Good

"The room was clean. Trying to find electric sockets behind the head of bed was difficult but doable, barely. Sometimes the toilet required a few attempts for complete emptying. Beds were clean and comfortable. No breakfast was served, as such, but there were a few munchies. I believe this motel had just been puchased, and there were signs of ongoing renovations that probably will result in much higher ratings in a month."

The Equinox Golf Resort & Spa

8/10 Good

"The room was nice and very clean. The bar and waitstaff were friendly and helpful. The biggest disappointment was the outdoor patio/fire pit area because management said that there was a problem with the gas line (but it's been out for at least a week or two), so it was dark and cold on the patio. They did nothing to help rectify the problem when in fact there were at least 30 people trying to enjoy the outdoors. Many requests were made for management to assist, but nothing. It took the friendly bar staff to come up with a solution. She grabbed lanterns from the inside tables to brighten up the darkness - this made people want to stay longer and enjoy drinks with friends. She made the difference that night! Her name started with a "P" and deserves recognition for making a decision that night."

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 high-speed (wired) Internet access. Keene Elm City Hotel, an Ascend Collection Hotel: Hotel, 1-minute walk from Green Mountain National Forest. Features complimentary bicycles, a seasonal outdoor pool and a 24-hour fitness centre. Kimpton Taconic Hotel by IHG: 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 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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