TOP Hotels with Pool in Chester, VT for 2026

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 : Offers a seasonal outdoor pool, an indoor pool and 4 restaurants. The Shire Woodstock : Provides complimentary high-speed (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

The Inn At Quail Run

Wilmington

Dive into summer luxury at this guesthouse's seasonal pool, complete with sauna and nearby bay views for a refreshing retreat.

Rp3.728.439 total

includes taxes & fees

11 May - 12 May

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

Hideaway Inn Mt. Snow

West Dover

Rp2.031.521 total

includes taxes & fees

12 May - 13 May

Hampton Inn Brattleboro

Brattleboro

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

Rp2.421.574 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.

Rp3.080.455 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.

Rp2.724.629 total

includes taxes & fees

1 Jun - 2 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.

Rp2.640.325 total

includes taxes & fees

26 May - 27 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.

Rp2.904.358 total

includes taxes & fees

11 May - 12 May

Black Mountain Inn

Brattleboro

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

Rp2.414.204 total

includes taxes & fees

13 May - 14 May

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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

"The property was clean, comfortable and quiet! We used the fitness room and wish we had brought suits for the pool. Good breakfast served, hot food too! Great hotel!"

On The River Inn

10/10 Excellent

"I booked a last minute reservation and was very pleasantly surprised. The hotel is beautiful! My room was large and I had a porch that looked out into a small pond and a park that had picnic tables. There were many areas throughout the hotel to socialize, including an outdoor area with a fire pit. Large game room in the second floor. Indoor pool on the ground level. Staff were friendly and professional. Highly recommend!"

Grand Summit Resort, A Vail Resorts Property

8/10 Good

"Rooms were very clean, great coffee in the room. The resort(the actual area in general )is in “mud month”. Very few restaurants and stores were open. Not the fault of the resort. Refrigerator needed to be requested. The views were spectacular and the lobby was beautiful "

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: Offers a seasonal outdoor pool, an indoor pool and 4 restaurants. The Shire Woodstock: Provides complimentary high-speed (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 such as DaVallia Art & Accents and Bonnie's Bundles Dolls. During your stay, visit sights such as Vermont Country Store, The Nature Museum and North Springfield Lake Recreation Area. 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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