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

Hotels with Swimming Pool in Chester, Vermont

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Check availability on Chester Hotels with Swimming Pool

Tonight
Aug 30 - Aug 31
Tomorrow
Aug 31 - Sep 1
Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13

Our top choices for Chester hotels with a pool

1. 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.
P7,229
P8,241 total
includes taxes & fees
Aug 31 - Sep 1
Pointe at Castle Hill Resort

2. 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.
P5,701
P6,328 total
includes taxes & fees
Sep 3 - Sep 4
The Upper Pass Lodge at Magic Mountain

3. 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.
P11,145
P12,260 total
includes taxes & fees
Aug 31 - Sep 1
Best Western Springfield Hotel

4. 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.
P9,277
P10,205 total
includes taxes & fees
Aug 31 - Sep 1
Blue Gentian Lodge at Magic Mountain

5. Hampton Inn Brattleboro

Hampton Inn Brattleboro
Brattleboro
  • Immerse in rejuvenating waters at this mountain-adjacent hotel featuring a pristine indoor pool and relaxing hot tub sanctuary.
P7,148
P7,863 total
includes taxes & fees
Sep 9 - Sep 10
Hampton Inn Brattleboro

6. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
  • Splash into comfort at this indoor pool oasis offering year-round aquatic escape in Keene.
P8,363
P9,074 total
includes taxes & fees
Sep 13 - Sep 14
Keene Elm City Hotel, an Ascend Collection Hotel

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.
P10,288
P12,500 total
includes taxes & fees
Sep 30 - Oct 1
Jackson Gore Village, A Vail Resorts Property

8. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
  • Relaxing indoor pool retreat with comfortable loungers sets the perfect stage for your Vermont ski getaway.
P7,356
P8,092 total
includes taxes & fees
Sep 6 - Sep 7
Comfort Inn & Suites Brattleboro I-91

9. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
  • Splash into luxury at this hotel's sparkling indoor pool, complete with plush sun loungers and serene atmosphere.
P9,277
P10,066 total
includes taxes & fees
Aug 31 - Sep 1
Best Western Plus Keene Hotel
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 Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent
"Nice room and property. With was down."
Amanda 1-night trip
Posted 16 hours ago
The Palmer House Resort, an Ascend Collection Hotel
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

10/10 Excellent
"First time stay here since we used to own a house in the area. Found the Inn comfortable and the amenities are amazing."
Maryalice 2-night trip
Posted 17 hours ago
The Equinox Golf Resort And Spa
On The River Inn

On The River Inn

10/10 Excellent
"This was one of the nicest hotels I have ever stayed in! We had a river view room with rocking chairs on the balcony, s’mores kits were offered every night (pick up by the front desk) and 2 fire pits to choose from. Game room was cute (although the air hockey table’s fan wasn’t strong on one side), library was absolutely gorgeous. Loved having water refilling stations on 2 of the 3 floors and 24/7 coffee/tea stations, too. Queen beds were very comfy, and the room was so spacious. I’d love another piece of furniture with drawers to keep our stuff though - we lived out of our suitcases because there was only an armoire with 3 half drawers. And maybe another towel bar or hooks in the bathroom to hang the towels to dry, especially if you have 4 people in a room. Breakfast buffet (included with our Expedia stay but extra for others) was always hot & fresh. We had 4 breakfasts: French toast, pancakes, waffles, french toast again. There was always fresh homemade pastries and muffins, yogurt, and oatmeal. I would have loved some fresh fruit like berries to go with the yogurt instead of apples and oranges. Staff was always so nice and helpful, especially at breakfast. Housekeeping forgot twice to give us the 4 fresh towels (gave 3 instead) but we got replacements when we asked at the desk."
Christopher 4-night trip
Posted 23 hours ago
On The River Inn
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

8/10 Good
"Has everything necessary for a two night stay."
Giovanna 2-night trip
Posted 2 days ago
Keene Elm City Hotel, an Ascend Collection Hotel
Bromley View Inn

Bromley View Inn

10/10 Excellent
"Beautiful cozy inn surrounded by trees and mountains. An incredible view with a cabin setting. Check-in was simple with coffee available 24/7"
Marvin 1-night trip
Posted 2 days ago
Bromley View Inn
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Very good breakfast, clean and spacious room, friendly staff."
William 2-night trip
Posted 3 days ago
Hampton Inn and Suites Manchester
Hampton Inn Brattleboro

Hampton Inn Brattleboro

8/10 Good
"Very clean. Good full breakfast."
Barbara 1-night trip
Posted 4 days ago
Hampton Inn Brattleboro
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

8/10 Good
"Clean room breakfast was good"
Lori 1-night trip
Posted 4 days ago
Best Western Plus Keene Hotel
Colonial Motel

Colonial Motel

8/10 Good
"X"
Steven 1-night trip
Posted 6 days ago
Colonial Motel

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. Kimpton Taconic Hotel by IHG: Hotel, 1-minute walk from Green Mountain National Forest. Offers complimentary bicycles, a seasonal outdoor pool, and a 24-hour fitness center. On The River Inn: Provides a children's pool, an indoor pool, and a sauna. Holiday Inn Club Vacations Mount Ascutney Resort by IHG: Offers buffet, an indoor pool, and complimentary wired internet access. Keene Elm City Hotel, an Ascend Collection Hotel: Hotel, 1-minute walk from Green Mountain National Forest. Features 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 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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