Find Hotels with a Pool in Chester, VT

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Top Chester Hotels with a Pool

Exterior
Historic 150-year-old farmhouse, Jacuzzi included

Historic 150-year-old farmhouse, Jacuzzi included

Chester Depot
  • Outdoor pool
  • Hot tub
9.8 out of 10, Exceptional, (9)
Poolside relaxation beckons at this 150-year-old farmhouse retreat where the well-maintained outdoor swimming area complements a rejuvenating hot tub. Guests appreciate premium bedding, fully equipped kitchen, and recreational amenities like tennis courts and a fitness center.
$389 nightly
The price is $436
Nov 17 - Nov 18
Total with taxes and fees
Historic 150-year-old farmhouse, Jacuzzi included
Indoor pool, sun loungers
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 star property
Brattleboro
  • Indoor pool
  • Pool loungers
8.6 out of 10, Excellent, (728)
Mountain adventures meet poolside relaxation at this Brattleboro hotel. Swimmers enjoy the indoor pool with plush sun loungers year-round, while winter enthusiasts appreciate easy access to cross-country and downhill skiing trails.
$104 nightly
The price is $115
Nov 17 - Nov 18
Total with taxes and fees
Comfort Inn & Suites Brattleboro I-91
Indoor pool
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 star property
Brattleboro
  • Indoor pool
  • Hot tub
8.2 out of 10, Very Good, (918)
Soothing waters welcome weary skiers and travelers in the immaculate indoor pool and hot tub area. Fitness enthusiasts appreciate the well-maintained exercise facility while enjoying proximity to local ski mountains, restaurants, and recreational activities.
$91 nightly
The price is $100
Dec 7 - Dec 8
Total with taxes and fees
Hampton Inn Brattleboro
Indoor pool, seasonal outdoor pool, sun loungers
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 star property
Manchester
  • Indoor pool
  • Pool loungers
  • Hot tub
7.4 out of 10, Good, (567)
Sparkling indoor and outdoor pools invite relaxation amid mountain scenery, complemented by soothing hot tub sessions. This luxury resort balances aquatic bliss with championship golf, tennis courts, and a full-service spa.
$162 nightly
The price is $179
Nov 16 - Nov 17
Total with taxes and fees
The Equinox Golf Resort & Spa
Indoor pool
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 star property
Keene
  • Indoor pool
8.4 out of 10, Very Good, (948)
Invigorating swims await at the pristine indoor pool, accessible from early morning until late evening. Guests praise the super comfortable beds, friendly staff, and excellent breakfast buffet at this well-located hotel near shopping and dining options.
$118 nightly
The price is $128
Dec 4 - Dec 5
Total with taxes and fees
Keene Elm City Hotel, an Ascend Collection Hotel
Indoor pool
Best Western Springfield Hotel

Best Western Springfield Hotel

2.5 star property
Springfield
  • Indoor pool
8.8 out of 10, Excellent, (799)
Sparkling waters await in the immaculately maintained indoor pool, offering a warm retreat after hiking nearby mountain trails or skiing at Okemo. Guests appreciate the family-friendly swimming environment complemented by an arcade room and spotless fitness center.
$143 nightly
The price is $157
Nov 23 - Nov 24
Total with taxes and fees
Best Western Springfield Hotel
Indoor pool
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 star property
Brattleboro
  • Indoor pool
8.8 out of 10, Excellent, (1003)
Splashing fun awaits in the indoor pool, open from 5 AM to 11 PM daily, complementing winter activities like nearby skiing and snowboarding. Families appreciate the arcade room while fitness enthusiasts enjoy the 24-hour gym.
$134 nightly
The price is $147
Nov 16 - Nov 17
Total with taxes and fees
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Indoor pool, open 6:00 AM to 10:00 PM, sun loungers
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3.0 star property
Keene
  • Indoor pool
  • Pool loungers
8.4 out of 10, Very Good, (1001)
Aquatic relaxation awaits at the pristine indoor pool, complete with comfortable loungers and convenient 6:00 AM to 10:00 PM access. Beyond swimming, guests praise the plentiful breakfast options, exceptionally clean rooms, and hiking trails nearby.
$149 nightly
The price is $162
Nov 16 - Nov 17
Total with taxes and fees
Best Western Plus Keene Hotel
Indoor pool
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

2.5 star property
Keene
  • Indoor pool
8.8 out of 10, Excellent, (343)
Swimmers glide through crystalline waters in the immaculate indoor pool, a cherished sanctuary regardless of season. Complementing this aquatic haven, the hotel boasts a 24-hour fitness center, billiards table, and highly praised complimentary breakfast buffet.
$158 nightly
The price is $171
Nov 24 - Nov 25
Total with taxes and fees
Hampton Inn & Suites Keene
Exterior
Black Mountain Inn

Black Mountain Inn

2.0 star property
Brattleboro
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
7.4 out of 10, Good, (474)
Cooling waters of the seasonal outdoor pool invite relaxation after exploring hiking trails and mountain biking routes. Garden views create a peaceful retreat while friendly staff ensure a comfortable stay at this quiet mountain escape.
$101 nightly
The price is $111
Dec 1 - Dec 2
Total with taxes and fees
Black Mountain Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chester Hotel Reviews

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Loved our room. Very clean and enjoyed fireplace. Only thing we were bothered by was noise outside our room probably connected to pool heater or filter."
Burton 2-night trip
Posted 2 days ago
Pointe at Castle Hill Resort

Frequently asked questions

What are some hotels with pools in Chester?
Woodstock Inn & Resort: Features a seasonal outdoor pool, an indoor pool, and 4 restaurants. The Shire Woodstock: Hotel, 15-minute walk from Okemo Mountain Resort. Provides an indoor pool, an outdoor pool, and 2 restaurants. Jackson Gore Village: Features complimentary bicycles, a seasonal outdoor pool, and a 24-hour fitness center. Kimpton Taconic Hotel by IHG: Features a full-service spa, an indoor pool, and free self parking. The Covered Bridge Inn: Offers a seasonal outdoor pool, an indoor pool, and 4 restaurants.
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 Grafton Historical Society, Vermont Country Store, and Plummer's Sugar House. 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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