A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

Find Hotels with a Pool in Chester, VT

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Check availability on Chester Hotels with a Pool

Tonight
Oct 11 - Oct 12
Tomorrow
Oct 12 - Oct 13
Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

Our top choices for Chester hotels with a pool

A two-story house with a front porch, a garage, and a well-maintained lawn.
A wooden staircase leading to a door with a wreath, a potted plant, and a framed picture on the wall.
A kitchen with a wooden island, stainless steel appliances, and a view of the outdoors through a window.
A hot tub in a forested area with a grill and a sign.

1. Historic 150-year-old farmhouse, Jacuzzi included

Historic 150-year-old farmhouse, Jacuzzi included
Chester Depot
  • Historic farmhouse offers year-round aquatic enjoyment with well-maintained outdoor pool and hot tub.
$388 nightly
$435 total
Nov 1 - Nov 2
Total with taxes and fees
Historic 150-year-old farmhouse, Jacuzzi included
An indoor swimming pool with four chairs and a hot tub.
A kitchen with wooden cabinets, a white microwave, a stove, and a refrigerator.
A spa named Castle Hill Spa with a well-maintained lawn and a pathway leading to the entrance.
A spacious lobby with a fireplace, leather seating, and a chandelier.

2. Pointe at Castle Hill Resort

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.
$169 nightly
$183 total
Oct 18 - Oct 19
Total with taxes and fees
Pointe at Castle Hill Resort
A swimming pool with a wooden deck and a red building in the background.
A bar area with a sign reading "MAGIC" and "featured Vermont beers".
A living room with a fireplace, a sofa, a coffee table, and a dining area with chairs and a table.
A restaurant with wooden tables and chairs, a central table with a sign reading "The Red Slate Restaurant", and large windows with views of the outside.

3. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
Londonderry
  • Slope-side sanctuary beckons with mountain vistas and a seasonal outdoor pool.
$100 nightly
$110 total
Oct 12 - Oct 13
Total with taxes and fees
The Upper Pass Lodge at Magic Mountain
An indoor swimming pool with clear water, lounge chairs, and a stone fireplace.
A hotel with a covered entrance, stone facade, and a sign indicating it is part of the Best Western chain.
A spacious, well-lit kitchen area with modern appliances, a central island with bar stools, and a chandelier.
A hotel room with a bed, a sofa, a coffee table, a desk, and a TV.

4. Best Western Springfield Hotel

Best Western Springfield Hotel
Springfield
  • Splash into mountain views at this hotel's warm indoor pool, perfect for year-round aquatic bliss.
$152 nightly
$167 total
Nov 1 - Nov 2
Total with taxes and fees
Best Western Springfield Hotel
A modern house with a pool, surrounded by lush greenery and mountains in the background.
A hot tub on a covered porch with a view of autumn foliage.
A snow-covered cabin with a large window, surrounded by trees and a mountain in the background.
A house with a balcony and a garden with red flowers.

5. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
Londonderry
  • Swim in the sunlit mountain waters at this alpine retreat's seasonal outdoor pool nestled in picturesque Vermont.
$149 nightly
$164 total
Nov 3 - Nov 4
Total with taxes and fees
Blue Gentian Lodge at Magic Mountain
A large stone building with a steep roof, surrounded by dense forest and hills.
A traditional bedroom with a four-poster bed, two armchairs, a wooden wardrobe, and a mirror.
A hotel room with a bed, a nightstand, a lamp, a door, and a view into another room with a couch and a window.
A spacious living room with a fireplace, comfortable seating, and a large window providing natural light.

6. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
$236 nightly
$257 total
Oct 19 - Oct 20
Total with taxes and fees
Castle Hill Resort And Spa
A hotel with a swimming pool area, including two hot tubs and lounge chairs.
A multi-story building with a stone patio, outdoor seating, and a fire pit.
A couple standing on a balcony with a view of a hotel courtyard.
A hotel with multiple buildings, a covered outdoor area, and a snowy landscape.

7. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
  • Dive into pool perfection at this mountain resort with year-round swimming and spa relaxation.
$204 nightly
$224 total
Nov 10 - Nov 11
Total with taxes and fees
Jackson Gore Village, A Vail Resorts Property
A rectangular swimming pool with a metal ladder, surrounded by a white fence, and shaded by trees.
A spacious room with high ceilings, wooden beams, large windows, and tables and chairs arranged for dining.
A cozy interior with a bar area, wooden furniture, and a Christmas tree.
An aerial view of a residential area with houses, a tennis court, and a swimming pool.

8. The Landgrove

The Landgrove
Londonderry
$176 nightly
$192 total
Oct 15 - Oct 16
Total with taxes and fees
The Landgrove
A bedroom with a fireplace, two beds, a chair, and a nightstand.
A green building with a wooden deck, a small porch, and a sign that reads 'Motel.'
A large, two-story house with a central entrance, surrounded by trees and a mountain backdrop.
A wooden deck with two chairs and a table, surrounded by a wooden railing, overlooking a grassy area with trees and a distant road.

9. The Manchester View

The Manchester View
Manchester Center
  • Mountain views from the pool create a picturesque escape at this serene Manchester retreat.
$113 nightly
$124 total
Nov 3 - Nov 4
Total with taxes and fees
The Manchester View
A swimming pool with a brick border and metal handrails.
A stone pathway leading to a porch with a wooden railing, surrounded by lush greenery and a lattice fence.
A room with a stone fireplace, large windows with curtains, a patterned rug, and a plush chair.
A large, white, two-story house with a steeply pitched roof, a balcony, and a staircase leading to the upper floor.

10. Windham Hill Inn

Windham Hill Inn
West Townshend
  • Serene seasonal outdoor pool offers 24-hour summer swimming amid Vermont's lush Windham Hills.
$207 nightly
$225 total
Oct 26 - Oct 27
Total with taxes and fees
Windham Hill Inn
View all properties

Choose what matters most at hotels with a pool in Chester

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Chester Hotel Reviews

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"Beautiful place for getaway!!!😊"
Esther 2-night trip
Posted 7 hours ago
The Black Bear Lodge at Stratton Mountain Resort
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent
"We stayed two nights, however they were booked at different times so we had to change rooms. Both rooms were excellent, but we preferred the main inn. We loved everything about this property. We’d love to learn to ski so we could return for a winter vacation. The tavern had great food. We highly recommend the cheese board. Also, we really appreciated the self-serve, free coffee, hot cocoa and flavor enhanced water! There is a little town very close for more restaurant option."
Traci 1-night trip
Posted 11 hours ago
Jackson Gore Village, A Vail Resorts Property
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

8/10 Good
"Nice facility. Clean and convenient."
Peter 2-night trip
Posted 13 hours ago
Pointe at Castle Hill Resort
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Great location and staff is AWESOME! Thanks for another pleasant stay!!"
Carey 1-night trip
Posted 1 day ago
Hampton Inn and Suites Manchester
The Manchester View

The Manchester View

10/10 Excellent
"We loved this property, our view opened up to magnificent Mountain View, if you are there during lead peeping season you know that makes a difference. We enjoyed the hot tub at night and the fireplace . Kind staff, they left cookies and bowls for our dog, breakfast was delicious, the variety of baked goods was perfect and the Vermont coffee provided brought up to a higher level I can’t wait to go back for a longer stay"
Cathya 1-night trip
Posted 1 day ago
The Manchester View
Colonial Motel

Colonial Motel

8/10 Good
"very convenient and cost was good, as we stay in Brattleboro as our daughter and granddaughter live in Turners Falls Mass. and its only a half hour drive to visit with them."
Leonard 3-night trip
Posted 2 days ago
Colonial Motel
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

8/10 Good
"Allen in the restaurant is great."
Bettina 1-night trip
Posted 4 days ago
Grand Summit Resort, A Vail Resorts Property
On The River Inn

On The River Inn

10/10 Excellent
"Karen at the front desk was absolutely delightful. She saw me struggling with my dog and bags, and helped me to my room. Dan on the housekeeping was so nice. We saw him almost every day. The hotel is incredibly pet friendly. It's so convenient to walk out of your room directly onto the rear lawn, and down toward the river. I had a nice chat with the lady who lives across the river. She also has a dog. The drive to downtown was just a few minutes. I highly recommend the farmer's market (you pass it on the way to downtown Woodstock). The room was very clean. The sink and bathroom door could use some updates, but other than that it was lovely. I would definitely return again with my pup."
VS 4-night trip
Posted 5 days ago
On The River Inn
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Beautiful location. Helpful staff"
Richard 1-night trip
Posted 12 days ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Frequently asked questions

What are some hotels with pools in Chester?
Fullerton Inn: Features a seasonal outdoor pool, an indoor pool, and 4 restaurants. Stone Hearth Inn and Eatery: Hotel, 1-minute walk from Green Mountain National Forest. Provides free self parking, a seasonal outdoor pool, and complimentary bicycles. Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area: Hotel, 1-minute walk from Green Mountain National Forest. Features daily, a seasonal outdoor pool, and free self parking. Woodstock Inn & Resort: Features a full-service spa, an indoor pool, and free self parking. The Jackson: Provides a children's pool, an indoor pool, and a sauna.
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 Connecticut River 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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