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
Aug 26 - Aug 27
Tomorrow
Aug 27 - Aug 28
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Our top choices for Chester hotels with a pool

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.
$428 nightly
$479 total
Sep 22 - Sep 23
Total with taxes and fees
Historic 150-year-old farmhouse, Jacuzzi included

2. 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.
$161 nightly
$177 total
Sep 2 - Sep 3
Total with taxes and fees
Best Western Springfield Hotel

3. 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.
$98 nightly
$106 total
Aug 30 - Aug 31
Total with taxes and fees
Pointe at Castle Hill Resort

4. 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.
$83 nightly
$92 total
Sep 27 - Sep 28
Total with taxes and fees
The Upper Pass Lodge at Magic Mountain

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.
$146 nightly
$161 total
Sep 1 - Sep 2
Total with taxes and fees
Blue Gentian Lodge at Magic Mountain

6. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
$239 nightly
$261 total
Aug 31 - Sep 1
Total with taxes and fees
Castle Hill Resort And Spa

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.
$199 nightly
$219 total
Sep 3 - Sep 4
Total with taxes and fees
Jackson Gore Village, A Vail Resorts Property

8. The Landgrove

The Landgrove
Londonderry
$179 nightly
$195 total
Sep 3 - Sep 4
Total with taxes and fees
The Landgrove

9. Echo Lake Inn

Echo Lake Inn
Plymouth
  • Outdoor tennis court meets poolside paradise at this charming bed and breakfast retreat.
$205 nightly
$224 total
Aug 31 - Sep 1
Total with taxes and fees
Echo Lake Inn

10. The Manchester View

The Manchester View
Manchester Center
  • Mountain views from the pool create a picturesque escape at this serene Manchester retreat.
$121 nightly
$133 total
Sep 10 - Sep 11
Total with taxes and fees
The Manchester View
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

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Would have liked a safe in my room. Rooms were large and clean."
Ruth 3-night trip
Posted 5 hours 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 7 hours ago
Hampton Inn Brattleboro
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"Very nice hotel off main road in and out of Manchester. Great outdoor porches to sit and relax. Free beverage coupons at social hour with free popcorn and pretzels. Staff friendly. Rooms very nice, spacious and beds very comfortable. Room temps were great. Free coffee in lobby area, free easy parking. $30 resort fee we didn't use any of the amenities. Walkable to shops and other nice restaurants."
mary ellen 1-night trip
Posted 9 hours ago
Kimpton Taconic Hotel by IHG
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

8/10 Good
"Clean room breakfast was good"
Lori 1-night trip
Posted 12 hours ago
Best Western Plus Keene Hotel
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"It was good!"
Ingrid 4-night trip
Posted 1 day ago
Keene Elm City Hotel, an Ascend Collection Hotel
The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent
"👍"
Chris 1-night trip
Posted 2 days ago
The Palmer House Resort, an Ascend Collection Hotel
Colonial Motel

Colonial Motel

8/10 Good
"X"
Steven 1-night trip
Posted 3 days ago
Colonial Motel
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

8/10 Good
"The place was clean and well maintained. Ample room and comfortable as well. Having a kitchen and having it properly equipped was a big plus."
Chris 2-night trip
Posted 4 days ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

10/10 Excellent
"We loved this hotel, really nice amenities, great rooms. I wish we had planned less activities and spent more time at the hotel. If you want to stay in the hotel, plan to spend a day in the hotel. Breakfast ends at 11 and bar closes at around 10 depending on crowd."
Gabriel 2-night trip
Posted 11 days ago
The Equinox Golf Resort & Spa

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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