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

Find Hotels with a Pool in Chestertown, NY

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Hotels with a Pool

Tonight
Oct 14 - Oct 15
Tomorrow
Oct 15 - Oct 16
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Chestertown hotels with a pool

An indoor swimming pool with clear water, surrounded by stone walls and wooden windows.
A terrace with outdoor seating, a view of a lake, and a dock.
A snow-covered lodge with cabins, a clear view of a lake, and mountains in the background.
A log cabin with a porch and a staircase leading to the entrance.

1. Lodges At Cresthaven

Lodges At Cresthaven
Lake George
  • Splash into relaxing bliss at this lakefront lodge with dual pools and private beach access.
$109 nightly
$121 total
Nov 8 - Nov 9
Total with taxes and fees
Lodges At Cresthaven
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.

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.
$109 nightly
$121 total
Oct 15 - Oct 16
Total with taxes and fees
The Juliana Resort
A swimming pool with a white fence, surrounded by lounge chairs and umbrellas.
A beach with rows of red chairs and a dock with boats.
An aerial view of a lakeside property with a dock, a gazebo, and a large house with a porch.
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 15 - Oct 16
Total with taxes and fees
Depe Dene Lakeside Resort
An indoor swimming pool with clear water, surrounded by lounge chairs and large windows.
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.
Two people sitting at a wooden table with a view of a lake and trees.

4. 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.
$181 nightly
$205 total
Nov 1 - Nov 2
Total with taxes and fees
Lodge at Schroon Lake
An indoor swimming pool area with lounge chairs, a lifeguard warning sign, and a clear view of the pool.
An outdoor patio with a fire pit, dining tables, chairs, and umbrellas.
A spacious lobby with a stone fireplace, blue seating, and a large chandelier.
A spacious dining area with a high ceiling, large windows, and a mix of seating arrangements including a bench and individual chairs.

5. 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
An indoor swimming pool with a brick floor, lounge chairs, and a stone wall.
A hotel lobby with a reception desk, seating area, stone fireplace, and large windows.
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.

6. 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 12 - Nov 13
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 table with a meal, a drink, and a view of the sea.
A bar area with a view of a lake and hills, a chalkboard menu, and a variety of bottles and glasses.
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.

7. 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 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.
$101 nightly
$112 total
Nov 4 - Nov 5
Total with taxes and fees
Comfort Inn & Suites Lake George
An indoor swimming pool with a glass ceiling, clear pool water, and a few chairs along the side.
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.
A compact hotel room with a kitchenette, a dining area, a bed, and a TV.

9. 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.
$93 nightly
$103 total
Oct 15 - Oct 16
Total with taxes and fees
Adirondack Retreat Inn & Suites
A hotel swimming pool with a tiled edge, a seating area with tables and chairs, and a small kiosk.
A hotel with a sign reading 'Best Western' and a parking lot with several cars.
A hotel room with a dining table, chairs, a television, a ceiling fan, and a large mirror.
A hotel room with two beds, a desk with a television, and a window with curtains.

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 21 - Oct 22
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

The Queensbury Hotel

The Queensbury Hotel

10/10 Excellent
"The breakfast was absolutely delicious!"
Sarah 2-night trip
Posted 13 hours ago
The Queensbury Hotel
Great Escape Lodge & Indoor Waterpark

Great Escape Lodge & Indoor Waterpark

8/10 Good
"Had to walk to far from checking in to my room! Room number was 305! My wife has Parkinson’s and it was very difficult for her to walk that distance!"
Thomas 1-night trip
Posted 16 hours ago
Great Escape Lodge & Indoor Waterpark
Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites

10/10 Excellent
"Lovely stay in Lake George. Great location, super easy walk to the main strip of Canada Street without being noisy at night. Parking was easy (no parallel parking) and it was easy to get in and out of the parking lot, accessible from two different streets. Supermarket is in walking distance."
Maija 2-night trip
Posted 18 hours ago
Adirondack Retreat Inn & Suites
Baymont by Wyndham Queensbury / Lake George

Baymont by Wyndham Queensbury / Lake George

8/10 Good
"My husband and I enjoyed our stay. The staff were professional. The room was spacious and clean. The bed was comfortable. The breakfast was okay. Enough to satisfy an appetite with eggs, waffles, bagels, yogurts, coffee muffins and tea. No meat served. The first floor hall has a heavy smell of what appeared to be cumin or curry. Carpets need a food shampoo. There was a smell of marijuana in the vestibule as we left. This is a good place ro stay but minor things mentioned should be addressed."
Jovie 1-night trip
Posted 19 hours ago
Baymont by Wyndham Queensbury / Lake George
Holiday Inn Resort Lake George - Adirondack Area by IHG

Holiday Inn Resort Lake George - Adirondack Area by IHG

8/10 Good
"When checking in we met Angus, very nice and helpful telling us where to go and what was happening that weekend that might interest us!"
Angel 3-night trip
Posted 19 hours ago
Holiday Inn Resort Lake George - Adirondack Area by IHG
The Georgian Lakeside Resort

The Georgian Lakeside Resort

8/10 Good
"The room was very clean and comfortable. All of the staff I talked to were friendly and helpful. My room didn't have a view of the lake. But only had to walk a minute or 2 to get to the water. At the end of the parking lot there is a hallway that gets you to the lake, the pool, and the pool bar. Nice views there and lots of chairs and outdoor type couches. About a 10-minute walk gets you to Shepard Park etc."
david 2-night trip
Posted 19 hours ago
The Georgian Lakeside Resort
Fort William Henry Hotel and Conference Center

Fort William Henry Hotel and Conference Center

8/10 Good
"Everything Breakfast staff I felt was a little slower then would have liked"
Margaret 1-night trip
Posted 21 hours ago
Fort William Henry Hotel and Conference Center
Friends Lake Inn

Friends Lake Inn

10/10 Excellent
"Friendly, warm, peaceful. Exactly what we were looking for."
william 1-night trip
Posted 2 days ago
Friends Lake Inn

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.

Explore a world of travel with Expedia