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

Chestertown Hotel Guide - Hotels with Pool in Chestertown, New York

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Check availability on Chestertown Hotels with Pool

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

Our top choices for Chestertown hotels with a pool

A swimming pool with a white fence, surrounded by lounge chairs and umbrellas.
A wooden deck with white railings leading to a lakeside view.
A modern living room with a sofa, coffee table, and artwork on the walls.
A beach with rows of red chairs and a dock with boats.

1. 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.
€97
includes taxes & fees
12 Oct - 13 Oct
Depe Dene Lakeside Resort
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 beach with white lounge chairs and a pier extending into the water.
A waterfront deck with lounge chairs, a sailboat, and a dock extending into calm water.

2. 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.
€108
includes taxes & fees
12 Oct - 13 Oct
The Juliana Resort
A poolside area with lounge chairs and umbrellas, a bar, and a view of the sea and mountains at night.
A bar area with a view of a lake and hills, a chalkboard menu, and a variety of bottles and glasses.
A table with a meal, a drink, and a view of the sea.
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.

3. 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.
€108
includes taxes & fees
11 Oct - 12 Oct
The Georgian Lakeside Resort
A pool area with a yellow water slide and a pool.
A spacious lobby with a curved staircase, a reception desk, and a decorative wall.
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.

4. 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.
€83
includes taxes & fees
1 Nov - 2 Nov
La Quinta Inn & Suites by Wyndham Lake George
An indoor swimming pool with a hot tub, seating area, and a door with an emergency exit sign.
A bathroom with a bathtub, toilet, and a towel rack with towels.
A hotel with a swimming pool, parking lot, and a view of a lake and mountains.
A hotel room with a large bed, a television on a dresser, a chair, and a door leading to another room.

5. Skyline Hotel Lake George

Skyline Hotel Lake George
Lake George
  • Splash into poolside paradise at Lake George with sun loungers and mountain views.
€72
includes taxes & fees
19 Oct - 20 Oct
Skyline Hotel Lake George
A swimming pool with chairs and tables around it, large windows, and a tiled floor.
Two people dining at an outdoor table with a pizza and drinks, overlooking a lake with a boat and hills in the background.
A hotel room with a bed, a chair, a small table, a lamp, and a balcony with a table and chairs.
A bar area with wooden chairs, a counter with a glass display, and hanging lights.

6. 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.
€123
includes taxes & fees
8 Nov - 9 Nov
Courtyard by Marriott 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.
An outdoor patio with a fire pit, dining tables, chairs, and umbrellas.
A spa area with a hot tub, seating, and a view of the outdoors.

7. 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 centre.
€100
includes taxes & fees
29 Oct - 30 Oct
Hampton Inn & Suites Lake George
A hotel pool area with lounge chairs and umbrellas, a clear sky, and a building with multiple windows.
A room with a wooden bench, a large tapestry, and a staircase leading to another room.
A spacious lobby with a high ceiling, a staircase, and a reception desk.
A hotel room with a large bed, a bench, a TV, and a window with curtains.

8. 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.
€100
includes taxes & fees
1 Nov - 2 Nov
Comfort Inn & Suites Lake George
An indoor swimming pool with clear water, surrounded by stone walls and wooden windows.
A lakeside lodge with a wooden exterior, a deck, and a row of beach chairs under umbrellas.
A terrace with outdoor seating, a view of a lake, and a dock.
A log cabin with a porch and a staircase leading to the entrance.

9. Lodges At Cresthaven

Lodges At Cresthaven
Lake George
  • Splash into relaxing bliss at this lakefront lodge with dual pools and private beach access.
€147
includes taxes & fees
9 Nov - 10 Nov
Lodges At Cresthaven
An indoor swimming pool with a glass ceiling, clear pool water, and a few chairs along the side.
A two-story motel with a balcony, a covered outdoor seating area, and a parking lot.
A patio with a mural of a landscape, outdoor seating, and a shaded area.
A cozy room with a large bed, a fireplace, a stone wall, and wooden beams on the ceiling.

10. Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites
Lake George
  • Splash into year-round fun with indoor and outdoor pools plus water toys for all ages.
€101
includes taxes & fees
11 Oct - 12 Oct
Adirondack Retreat Inn & Suites
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

8/10 Good
"Breakfast wasn’t very good"
Robert 1-night trip
Posted 16 hours ago
Baymont by Wyndham Queensbury / Lake George
Friends Lake Inn

Friends Lake Inn

8/10 Good
"The staff were very helpful and friendly. The amenities should be improved and the bathroom shower and tiles should be cleaner."
william 1-night trip
Posted 17 hours ago
Friends Lake Inn
Fort William Henry Hotel and Conference Center

Fort William Henry Hotel and Conference Center

10/10 Excellent
"Side building are motel style with stairs, thin walls, carpet has moisture smell, otherwise clean rooms, plenty of parking."
Cai Peng 1-night trip
Posted 17 hours ago
Fort William Henry Hotel and Conference Center
Surfside On The Lake

Surfside On The Lake

8/10 Good
"Stayed here during a wedding weekend. The room was a little dated, but was clean and had the essential amenities for our stay. We arrived early and were allowed to check in as soon as we arrived (four hours ahead of the official check in time)."
Michelle 2-night trip
Posted 22 hours ago
Surfside On The Lake
Great Escape Lodge & Indoor Waterpark

Great Escape Lodge & Indoor Waterpark

8/10 Good
"Great value in the area to be honest. Great price compared to other options in the area. Very convenient location to Lake George and the Worlds Biggest Garage Sale."
Brian 2-night trip
Posted 22 hours ago
Great Escape Lodge & Indoor Waterpark
Holiday Inn Resort Lake George - Adirondack Area by IHG

Holiday Inn Resort Lake George - Adirondack Area by IHG

8/10 Good
"This property is very well-maintained and clean. Their rooms are fresh and updated and the property looks relaxing and inviting. We didn’t really use any of the amenities, but it was well situated. The only thing I would say is if you’re looking for something on the water or with water views, this is not the property for you. Other than that, it’s well worth a visit."
Eric 2-night trip
Posted 2 days ago
Holiday Inn Resort Lake George - Adirondack Area by IHG
Country Inn & Suites by Radisson, Lake George (Queensbury), NY

Country Inn & Suites by Radisson, Lake George (Queensbury), NY

10/10 Excellent
"We really enjoyed our stay here. The room was very clean and comfortable with some updates. The carpet in the main hallways could do with updating. The breakfast was delicious with several options. Snacks and a bottle of water were given free as extras. In all it was a good location for a variety of restaurants and shopping, and to visit Lake George."
Kathleen 1-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Lake George (Queensbury), NY
The Georgian Lakeside Resort

The Georgian Lakeside Resort

8/10 Good
"Room was sparkling clean but the smell of the cleaning chemicals vas very strong in the air that gave us both headache. Even after airing the room, the smell lingered around."
Monika 3-night trip
Posted 3 days ago
The Georgian Lakeside Resort

Frequently asked questions

What are some hotels with pools in Chestertown?
Pine Tree Motel & Cabins: Offers sunloungers, 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, visit 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 the local weather in Chestertown into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chestertown are January, March, November and December, with each month seeing an average of 33 cm of snowfall.