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

Find Hotels with a Pool in Chester, VT

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chester Hotels with a Pool

Tonight
4 Oct - 5 Oct
Tomorrow
5 Oct - 6 Oct
Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

Our top choices for Chester hotels with a pool

A two-story house with a porch, a small garden, and a well-maintained lawn.
A kitchen with a coffee maker, mugs, and containers labeled 'Sugar' and 'Coffee'.
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.
AED 680
AED 1,798 total
includes taxes & fees
26 Oct - 27 Oct
Historic 150-year-old farmhouse, Jacuzzi included
An indoor swimming pool with clear water, lounge chairs, and a stone fireplace.
A spacious, well-lit kitchen area with modern appliances, a central island with bar stools, and a chandelier.
A hotel with a covered entrance, stone facade, and a sign indicating it is part of the Best Western chain.
A hotel room with a bed, a sofa, a coffee table, a desk, and a TV.

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.
AED 559
AED 615 total
includes taxes & fees
1 Nov - 2 Nov
Best Western Springfield Hotel
An indoor swimming pool with four chairs and a hot tub.
A sign for Castle Hill Spa surrounded by lush greenery and a well-maintained lawn.
A spacious lobby with a fireplace, leather seating, and a chandelier.
A kitchen with wooden cabinets, a white microwave, a stove, and a refrigerator.

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.
AED 542
AED 618 total
includes taxes & fees
21 Oct - 22 Oct
Pointe at Castle Hill Resort
A large stone building with a steep roof, surrounded by dense forest and hills.
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 traditional bedroom with a four-poster bed, two armchairs, a wooden wardrobe, and a mirror.
A spacious living room with a fireplace, red sofas, a wooden coffee table, and a television.

4. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
AED 820
AED 894 total
includes taxes & fees
19 Oct - 20 Oct
Castle Hill Resort And Spa
A swimming pool with a wooden deck and a red building in the background.
A living room with a fireplace, a sofa, a coffee table, and a dining area with chairs and a table.
A Christmas tree decorated with lights, ornaments, and a bow.
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.

5. 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.
AED 398
AED 456 total
includes taxes & fees
3 Nov - 4 Nov
The Upper Pass Lodge at Magic Mountain
A hotel with a swimming pool area, including two hot tubs and lounge chairs.
A hotel with multiple buildings, a covered outdoor area, and a snowy landscape.
A golf course with rolling hills, trees, and a distant mountain range.
A couple standing on a balcony with a view of a hotel courtyard.

6. 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.
AED 662
AED 804 total
includes taxes & fees
26 Oct - 27 Oct
Jackson Gore Village, A Vail Resorts Property
A modern house with a pool, surrounded by lush greenery and mountains in the background.
A house with a balcony and a garden with red flowers.
A snow-covered cabin with a large window, surrounded by trees and a mountain in the background.
A sunroom with a round table covered by a plaid tablecloth, surrounded by chairs, large windows offering a view of a garden and pond.

7. 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.
AED 547
AED 602 total
includes taxes & fees
1 Nov - 2 Nov
Blue Gentian Lodge at Magic Mountain
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.
An aerial view of a residential area with houses, a tennis court, and a swimming pool.
A large two-story house with a front porch and a well-maintained lawn.

8. The Landgrove

The Landgrove
Londonderry
AED 790
AED 861 total
includes taxes & fees
1 Nov - 2 Nov
The Landgrove
A swimming pool with a brick border and metal handrails.
A kitchen with wooden cabinets, a built-in stove, a microwave, and a sink.
A large, white, two-story house with a steeply pitched roof, a balcony, and a staircase leading to the upper floor.
A stone pathway leading to a porch with a wooden railing, surrounded by lush greenery and a lattice fence.

9. Windham Hill Inn

Windham Hill Inn
West Townshend
  • Serene seasonal outdoor pool offers 24-hour summer swimming amid Vermont's lush Windham Hills.
AED 683
AED 744 total
includes taxes & fees
20 Oct - 21 Oct
Windham Hill Inn
A bedroom with a fireplace, two beds, a chair, and a nightstand.
A large, two-story house with a central entrance, surrounded by trees and a mountain backdrop.
A green building with a wooden deck, a small porch, and a sign that reads 'Motel.'
A living room with a fireplace, a sofa, a coffee table, and a view through a sliding glass door.

10. The Manchester View

The Manchester View
Manchester Center
  • Mountain views from the pool create a picturesque escape at this serene Manchester retreat.
AED 310
AED 341 total
includes taxes & fees
3 Nov - 4 Nov
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

Colonial Motel

Colonial Motel

10/10 Excellent
"clean room"
Biplob 1-night trip
Posted 3 hours ago
Colonial Motel
Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Dinner at their restaurant was very good- the best fish(halibut) I’ve ever had. The rooms are small but very clean and decorated with thought. The continental breakfast was also very good. The staff was helpful and friendly. We enjoyed our stay very much."
Delletta 1-night trip
Posted 8 hours ago
Woodstock Inn & Resort
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"Great room at a reasonable price , Nice staff, and very clean facilities."
Anthony 1-night trip
Posted 9 hours ago
The Black Bear Lodge at Stratton Mountain Resort
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Very nice place, quiet and easily accessible. Room was large with separate large bedroom with door. Large LR with fireplace, sofa & recliner and fully stocked kitchen."
Mary 2-night trip
Posted 2 days ago
Pointe at Castle Hill Resort
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent
"My daughter and I were looking for someplace to meet in the middle… one coming from upstate New York and one coming from Massachusetts.This was not the first hotel we looked at. Fortunately it is the one we stayed at! The facility is very nice, even though older still very well maintained. Staff was exceptional! The location was perfect for just a fun getaway weekend. The downtown area has some lovely restaurants and shops but the restaurant at the resort was also very good. We enjoyed the area so much. We're talking about going again in the winter, even though neither of us have skied in ages!"
Michelle 3-night trip
Posted 2 days ago
Jackson Gore Village, A Vail Resorts Property
On The River Inn

On The River Inn

8/10 Good
"We had a river view suite. Trouble was you couldn’t see the river. There was to much undergrowth and trees, so you couldn’t tell there was a river there. The view from our balcony was beautiful, out onto the large lawn and a small pond. The TVs are old, so you couldn’t stream. Make sure you tell the front desk or put out your door hanger or you won’t get your room refreshed. The bar seemed open only during dinner hours. During our stay, one night the chief was “out” and they only served burgers. Breakfast was around $18, we never went down. Our room was large and bathroom adequate. It’s a 10 minute drive to town. It’a satisfactory hotel, but not worth the price."
Loxley 3-night trip
Posted 3 days ago
On The River Inn
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

10/10 Excellent
"Our “go to” for an uber relaxing and comfortable getaway when we are seeking the amenities of an established hotel."
Deborah 1-night trip
Posted 4 days ago
The Equinox Golf Resort And Spa
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 5 days ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

8/10 Good
"What I like is the room was well stocked, very clean and the staff is very helpful. What I did not like is the parking is very inconvenient and is quite a walk which is never fun in bad weather. They need more luggage carts. It looked like they have about 5 or 6 for about a 200 room hotel. There was only one place on the property to get breakfast in the morning. There is a stove and refrigerator in the room. I had no idea before hand those would be available!"
Richard 2-night trip
Posted 7 days ago
Grand Summit Resort, A Vail Resorts Property

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.

Explore a world of travel with Expedia