A waterfront town with a pier, dock, and several buildings.

Find Hotels with a Pool in Chestertown, NY

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Check availability on Chestertown Hotels with a Pool

Tonight
Oct 7 - Oct 8
Tomorrow
Oct 8 - Oct 9
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Chestertown hotels with a pool

A pool area with lounge chairs and umbrellas, surrounded by trees and a view of a lake.
A living room with a stone fireplace, leather furniture, and a chandelier.
A waterfront deck with lounge chairs, a sailboat, and a dock extending into calm water.
A beach with white lounge chairs and a pier extending into the water.

1. The Juliana Resort

The Juliana Resort
Diamond Point
  • Dive into poolside bliss at this Lake George hotel with a sparkling outdoor pool and private beach access.
$92 nightly
$102 total
Oct 8 - Oct 9
Total with taxes and fees
The Juliana Resort
An indoor swimming pool with clear water, surrounded by lounge chairs and large windows.
A row of cabins with balconies, a well-maintained lawn, and a lake view.
A log cabin with a wooden porch and stone walls, surrounded by a well-maintained garden with various plants and flowers.
A dining area with a table set for four, large windows offering a view of a lake and trees, and a stone wall in the background.

2. Lodge at Schroon Lake

Lodge at Schroon Lake
Schroon Lake
  • Refreshing aquatic escape awaits at this lakeside hotel with an inviting indoor pool and hot tub sanctuary.
$168 nightly
$189 total
Nov 1 - Nov 2
Total with taxes and fees
Lodge at Schroon Lake
A swimming pool with a white fence, surrounded by lounge chairs and umbrellas.
An aerial view of a lakeside property with a dock, a gazebo, and a large house with a porch.
A beach with rows of red chairs and a dock with boats.
A modern living room with a sofa, coffee table, and artwork on the walls.

3. Depe Dene Lakeside Resort

Depe Dene Lakeside Resort
Lake George
  • Soak in crystal blue waters at this lakeside resort with a seasonal heated pool and sun-filled beach days.
$109 nightly
$121 total
Oct 12 - Oct 13
Total with taxes and fees
Depe Dene Lakeside Resort
An indoor swimming pool with a brick floor, lounge chairs, and a stone wall.
A hotel with a covered entrance, large windows, and a parking lot.
A spacious living area with a stone fireplace, comfortable seating, a large window with a view, and a chandelier.
A hotel lobby with a reception desk, seating area, stone fireplace, and large windows.

4. Holiday Inn Resort Lake George - Adirondack Area by IHG

Holiday Inn Resort Lake George - Adirondack Area by IHG
Lake George
  • Pool paradise awaits with year-round swimming options at this mountain resort hotel.
$112 nightly
$124 total
Nov 4 - Nov 5
Total with taxes and fees
Holiday Inn Resort Lake George - Adirondack Area by IHG
A poolside area with lounge chairs and umbrellas, a bar, and a view of the sea and mountains at night.
A view from a room with a window overlooking a lakeside patio area with tables and chairs, a covered seating area, and a white railing along the water's edge.
A bar area with a view of a lake and hills, a chalkboard menu, and a variety of bottles and glasses.
A marina with docked boats, a covered seating area, and a view of a lake with mountains in the background.

5. The Georgian Lakeside Resort

The Georgian Lakeside Resort
Lake George
  • Relax by the seasonal outdoor pool with a signature cocktail and lakefront vistas, then retreat to your private beachfront oasis.
$98 nightly
$109 total
Oct 15 - Oct 16
Total with taxes and fees
The Georgian Lakeside Resort
A hotel pool area with lounge chairs and umbrellas, a clear sky, and a building with multiple windows.
A hotel room with a large bed, a bench, a TV, and a window with curtains.
A hotel entrance with a stone facade, a covered entrance area, and a landscaped driveway.
A spacious lobby with a high ceiling, a staircase, and a reception desk.

6. Comfort Inn & Suites Lake George

Comfort Inn & Suites Lake George
Lake George
  • Year-round aquatic adventures await with indoor and seasonal outdoor pools for every season.
$101 nightly
$112 total
Nov 1 - Nov 2
Total with taxes and fees
Comfort Inn & Suites Lake George
A pool area with a yellow water slide and a pool.
A hotel room with a large bathtub, a bed with white bedding, a dark headboard, and a black and white patterned floor.
A hotel with a prominent 'LAQUINTA' sign, a covered entrance, and a parking lot.
A spacious lobby with a Christmas tree, seating area, and a spiral staircase.

7. La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George
Lake George
  • Splash into family fun at this Lake George hotel with an indoor pool, waterslide, and hot tub.
$84 nightly
$93 total
Oct 28 - Oct 29
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Lake George
An indoor swimming pool area with lounge chairs, a lifeguard warning sign, and a clear view of the pool.
A spacious dining area with a high ceiling, large windows, and a mix of seating arrangements including a bench and individual chairs.
A spa area with a hot tub, seating, and a view of the outdoors.
A spacious lobby with a stone fireplace, blue seating, and a large chandelier.

8. Hampton Inn & Suites Lake George

Hampton Inn & Suites Lake George
Lake George
  • Plunge into relaxation at this family-friendly retreat with an inviting indoor pool, hot tub, and well-equipped fitness center.
$101 nightly
$112 total
Oct 29 - Oct 30
Total with taxes and fees
Hampton Inn & Suites Lake George
A swimming pool with chairs and tables around it, large windows, and a tiled floor.
A hotel room with a bed, a chair, a small table, a lamp, and a balcony with a table and chairs.
A room with a balcony, a sofa, a table, and a lamp.
A bar area with wooden chairs, a counter with a glass display, and hanging lights.

9. Courtyard by Marriott Lake George

Courtyard by Marriott Lake George
Lake George
  • Dive into aquatic bliss at this hotel's indoor pool sanctuary, open year-round regardless of weather.
$129 nightly
$143 total
Nov 4 - Nov 5
Total with taxes and fees
Courtyard by Marriott Lake George
A hotel pool area with multiple pools, lounge chairs, and a covered seating area.
A dining area with a table and chairs, a kitchen area with a microwave and stove, and a television in the living room.
A compact kitchen with wooden cabinets, a white refrigerator, a microwave, and a coffee maker on the countertop.
A hotel room with a bed, a desk with a television, a chair, a desk lamp, a mirror, and a framed picture on the wall.

10. Skyline Hotel Lake George

Skyline Hotel Lake George
Lake George
  • Splash into poolside paradise at Lake George with sun loungers and mountain views.
$72 nightly
$80 total
Oct 14 - Oct 15
Total with taxes and fees
Skyline Hotel Lake George
View all properties

Choose what matters most at hotels with a pool in Chestertown

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Chestertown Hotel Reviews

Baymont by Wyndham Queensbury / Lake George

Baymont by Wyndham Queensbury / Lake George

10/10 Excellent
"Clean room and breakfast"
Prathamesh 3-night trip
Posted 4 hours ago
Baymont by Wyndham Queensbury / Lake George
Lakefront Terrace Resort

Lakefront Terrace Resort

10/10 Excellent
"We got one of the best rooms with 2 huge windows to the lake, it was amazing! Private beach was another great thing about the hotel. We will definitely come back in the summer."
Victoria 2-night trip
Posted 5 hours ago
Lakefront Terrace Resort
The Georgian Lakeside Resort

The Georgian Lakeside Resort

10/10 Excellent
"C'était bien, honnêtement j'ai trouvé genre 2-3 cheveux et c'est pas mal ça. La trappe d'air au plafotde la salle de bain était entrain de se casser la figure et mangeait la poussière mais tout le reste était parfait. Le lit était Super confortable!!"
Marie-Pier 1-night trip
Posted 10 hours ago
The Georgian Lakeside Resort
The Queensbury Hotel

The Queensbury Hotel

8/10 Good
"Cool old hotel. Would give it 5 stars but for the leaf blowing at 6 am."
Kim 1-night trip
Posted 12 hours ago
The Queensbury Hotel
Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites

8/10 Good
"It was beautiful and the hot tub in the room was heavenly"
Harold 2-night trip
Posted 14 hours ago
Adirondack Retreat Inn & Suites
Surfside On The Lake

Surfside On The Lake

8/10 Good
"For a queen bed it felt more like a full size. The room was very clean. When I asked about the size of the bed the front desk didn't really know what I was talking about I have a queen bed. Definitely felt more like a full size maybe a small Queen I don't know. We were parked out by the pool and there was no parking next to our room which was kind of inconvenient. We had somebody with us and they had to park down the road even though it was off season and there were parking places all over the hotel they still made you park a mile down the road any extra cars I can see on season where maybe one car per room I could see it's limited parking but when nobody's there why make somebody go that far. Didn't make sense. But overall it was a pleasant stay very convenient to downtown. If they had minor tweaks at certain times of the year and maybe upgrade the size of their beds. That would be more of a selling point because of that I probably won't be going back because it wasn't very accommodating with the parking window was plenty of it so that's enough for me to say I would go somewhere else in the future."
Michael 2-night trip
Posted 2 days ago
Surfside On The Lake
Fort William Henry Hotel and Conference Center

Fort William Henry Hotel and Conference Center

10/10 Excellent
"Great place and views of the lake!"
Jason 4-night trip
Posted 2 days ago
Fort William Henry Hotel and Conference Center

Frequently asked questions

What are some hotels with pools in Chestertown?
Pine Tree Motel & Cabins: Offers sun loungers, a pool, and complimentary wireless internet access. Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.: Hotel located near Great Escape. Features buffet, an indoor pool, and free self parking. Great Escape Lodge & Indoor Waterpark: Hotel, 1-minute walk from Lake George. Offers a private beach, a seasonal outdoor pool, and free self parking. La Quinta Inn & Suites by Wyndham Lake George: Features 2 restaurants, an indoor pool, and 2 bars. The Georgian Lakeside Resort: Hotel located near Great Escape. Offers daily, an indoor pool, and free self parking.
What is there to see and do in Chestertown?
The picturesque setting of Loon Lake Beach and Friends Lake showcase the area's natural beauty. During your stay, check out sights such as Loon Lake, Hudson River, and Tripp Pond. Take in the natural beauty of Chestertown with the lakeside setting.
When is the best time to book a hotel with a pool in Chestertown?
Taking into account the local weather in Chestertown 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 Chestertown are January, March, November, and December, with each month seeing an average of 13 inches of snowfall.

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