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
Sep 22 - Sep 23
Tomorrow
Sep 23 - Sep 24
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Chestertown hotels with a pool

A swimming pool area with lounge chairs and umbrellas, surrounded by a white fence, overlooking a lake and forested hills.
A two-story house with a porch, multiple windows, and hanging flower baskets.
A residential area with a hanging flower basket, houses, and a lake in the background.
A room with a large window overlooking a lake and hills, a table with a remote control, and a hanging lamp.

1. Nordick's Inn

Nordick's Inn
Lake George
  • Dive into poolside bliss at this Lake George motel with seasonal outdoor pool and tranquil terrace.
$85 nightly
$94 total
Sep 23 - Sep 24
Total with taxes and fees
Nordick's Inn
A pool area with lounge chairs and umbrellas, surrounded by trees and a view of a lake.
A lakeside patio with wooden chairs, a fire pit, and boats in the background.
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.

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.
$92 nightly
$102 total
Sep 23 - Sep 24
Total with taxes and fees
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 marina with docked boats, a covered seating area, and a view of a lake with mountains in the background.
A table with a meal, a drink, and a view of the sea.

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.
$100 nightly
$111 total
Sep 23 - Sep 24
Total with taxes and fees
The Georgian Lakeside Resort
A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.
A wooden bear sculpture with a sign reading "Admiral Motel" in front of a building with outdoor seating.
A poolside area with a blue sofa, white wicker chairs, and a small table with a basket.
A reception area with a wooden counter, a welcome sign, and a ship's wheel decoration.

4. Admiral Motel

Admiral Motel
Lake George
  • Splash into lakeside bliss at this clean motel with a seasonal outdoor pool and cozy loungers.
$87 nightly
$97 total
Sep 23 - Sep 24
Total with taxes and fees
Admiral Motel
A bathroom with a sink, mirror, towel rack, shower, and toilet.
A reception area with a counter, seating, a TV, and informational posters.
A reception area with a wooden reception desk, a bulletin board with travel brochures, and a wooden floor.
A two-story building with a sign reading "Howard Johnson."

5. Howard Johnson by Wyndham Lake George

Howard Johnson by Wyndham Lake George
Lake George
  • Splash into vacation mode at this Lake George gem with a sun-drenched pool.
$75 nightly
$83 total
Sep 23 - Sep 24
Total with taxes and fees
Howard Johnson by Wyndham Lake George
A dining area with multiple tables and chairs, chandeliers, and large windows with a view of a lake.
A hotel with multiple floors, a parking lot, and a view of a body of water.
A river with a large white boat docked at a pier, surrounded by autumn-colored trees and buildings in the background.

6. Fort William Henry Hotel and Conference Center

Fort William Henry Hotel and Conference Center
Lake George
  • Refreshing lake views paired with year-round swimming options make this resort perfect for water lovers seeking mountain scenery.
$98 nightly
$109 total
Oct 14 - Oct 15
Total with taxes and fees
Fort William Henry Hotel and Conference Center
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 entrance with a stone facade, a covered entrance area, and a landscaped driveway.

7. 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.
$119 nightly
$132 total
Oct 19 - Oct 20
Total with taxes and fees
Comfort Inn & Suites Lake George
A swimming pool with green lounge chairs and a white picket fence.
A building with a sign reading "The Heritage of La".
A white building with a covered porch and a gazebo with flower baskets.
A covered outdoor seating area with two green lounge chairs, a tree with pink flowers, and a parking area in the background.

8. Heritage of Lake George

Heritage of Lake George
Lake George
  • Dive into sparkling waters at this family-friendly lake motel with heated outdoor pool.
$89 nightly
$99 total
Sep 23 - Sep 24
Total with taxes and fees
Heritage of Lake George
An indoor swimming pool with a glass ceiling, clear pool water, and a few chairs along the side.
A compact hotel room with a kitchenette, a dining area, a bed, and a TV.
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.

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.
$88 nightly
$98 total
Oct 5 - Oct 6
Total with taxes and fees
Adirondack Retreat Inn & Suites

10. Lakefront Terrace Resort

Lakefront Terrace Resort
Lake George
  • Serene lakeside retreat offers pristine heated pool and private beach, perfect for unwinding amid spectacular mountain views.
$81 nightly
$90 total
Oct 4 - Oct 5
Total with taxes and fees
Lakefront Terrace Resort
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

Super 8 by Wyndham Lake George/Downtown

Super 8 by Wyndham Lake George/Downtown

10/10 Excellent
"All ok"
Dany 1-night trip
Posted 1 hour ago
Super 8 by Wyndham Lake George/Downtown
Lakefront Terrace Resort

Lakefront Terrace Resort

8/10 Good
"Good room product overall, could do with some deep cleaning esp the bathroom. the sink faucet was way too high so the whole time we had to use towels to keep the counter and floors dry. But good quaint lake view room."
MST 2-night trip
Posted 10 hours ago
Lakefront Terrace Resort
Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites

8/10 Good
"The room was clean and the property was well taken care of"
Trinity 3-night trip
Posted 12 hours ago
Adirondack Retreat Inn & Suites
The Queensbury Hotel

The Queensbury Hotel

10/10 Excellent
"beautifully remodeled building. Close to restaurants."
Sharon 1-night trip
Posted 18 hours ago
The Queensbury Hotel
Holiday Inn Resort Lake George - Adirondack Area by IHG

Holiday Inn Resort Lake George - Adirondack Area by IHG

8/10 Good
"Great place to stay while in Lake George. Older property that has been updated well."
James 2-night trip
Posted 22 hours ago
Holiday Inn Resort Lake George - Adirondack Area by IHG
Tiki Resort

Tiki Resort

8/10 Good
"The room was updated nicely including a nice bathroom and shower. Beds were nice and all furniture in the room were new. Just 2 areas for improvements. The WIFI does not work in the rooms that are detached from the main building. Every time you try to connect the same message comes up and says cannot connect to WIFI at the time. Yet when you go into the main building you hook up right away. All that is needed is a repeater if proper strength attached to the building of rooms to correct this problem. This was the same problem the last time it stayed there. The other problem is it appears that the floors are not mopped after each stay. The evidence was I dropped a bit of water on the floor. I took a tissue to dry it up and the tissue turned black. We had just checked into the room. There is no reason why after each stay the main traffic areas which is very small is not properly mopped to keep the floor clean. No other issues."
Louis 2-night trip
Posted 22 hours ago
Tiki Resort
Great Escape Lodge & Indoor Waterpark

Great Escape Lodge & Indoor Waterpark

10/10 Excellent
"Everything was great ..EXCEPT the Starbucks Cafe is not serving Starbucks coffee for $6 a cup. Lol.. its cheap brewed coffee and I dont know how they get away with it."
eva 2-night trip
Posted 22 hours ago
Great Escape Lodge & Indoor Waterpark

Frequently asked questions

What are some hotels with pools in Chestertown?
Pine Tree Motel & Cabins: Hotel located near Great Escape. Provides buffet, an indoor pool, and free self parking. Great Escape Lodge & Indoor Waterpark: Hotel, 1-minute walk from Lake George. Features a private beach, a seasonal outdoor pool, and free self parking. La Quinta Inn & Suites by Wyndham Lake George: Offers 2 restaurants, an indoor pool, and 2 bars. The Georgian Lakeside Resort: Hotel located near Great Escape. Features daily, an indoor pool, and free self parking. The Queensbury Hotel: Offers an indoor pool, an outdoor pool, and free self parking.
What is there to see and do in Chestertown?
The picturesque setting of Friends Lake and Loon Lake showcase the area's natural beauty. During your stay, check out sights such as Hudson River, Loon Lake Beach, 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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