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
Aug 30 - Aug 31
Tomorrow
Aug 31 - Sep 1
Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13

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 beach with white lounge chairs and a pier extending into the water.
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.

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.
$102 nightly
$113 total
Sep 23 - Sep 24
Total with taxes and fees
The Juliana Resort
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 two-story motel with a balcony, a covered outdoor seating area, and a parking lot.

2. 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.
$90 nightly
$100 total
Sep 1 - Sep 2
Total with taxes and fees
Adirondack Retreat Inn & Suites
A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.
A white building with a yellow awning, a porch with flowers, and American flags.
A wooden bear sculpture with a sign reading "Admiral Motel" in front of a building with outdoor seating.
A reception area with a wooden counter, a welcome sign, and a ship's wheel decoration.

3. Admiral Motel

Admiral Motel
Lake George
  • Splash into lakeside bliss at this clean motel with a seasonal outdoor pool and cozy loungers.
$79 nightly
$88 total
Sep 22 - Sep 23
Total with taxes and fees
Admiral Motel
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 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 marina with docked boats, a covered seating area, and a view of a lake with mountains in the background.

4. 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.
$107 nightly
$119 total
Sep 22 - Sep 23
Total with taxes and fees
The Georgian Lakeside Resort
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 wooden deck with white railings leading to a lakeside view.

5. 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
Sep 20 - Sep 21
Total with taxes and fees
Depe Dene Lakeside Resort

6. 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.
$88 nightly
$98 total
Sep 30 - Oct 1
Total with taxes and fees
Lakefront Terrace Resort
A swimming pool with green lounge chairs and a white picket fence.
A bathroom with a window, sink, mirror, and towel rack.
A white building with a covered porch and a gazebo with flower baskets.
A building with a sign reading "The Heritage of La".

7. Heritage of Lake George

Heritage of Lake George
Lake George
  • Dive into sparkling waters at this family-friendly lake motel with heated outdoor pool.
$90 nightly
$100 total
Sep 3 - Sep 4
Total with taxes and fees
Heritage of Lake George
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 row of cabins with balconies, a well-maintained lawn, and a lake view.
Two people sitting at a wooden table with a view of a lake and trees.

8. 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
Sep 7 - Sep 8
Total with taxes and fees
Lodge at Schroon Lake
A hotel with a pool, beach chairs, umbrellas, and a view of the lake.
A lakeside beach with rows of beach chairs and a dock with boats.
A beachside seating area with a fire pit surrounded by chairs and red umbrellas, overlooking a lake with mountains in the background.
A log cabin-style building with a metal roof, stone pillars, and a glass door entrance.

9. Scotty's Lakeside Resort

Scotty's Lakeside Resort
Lake George
  • Splash into lakeside fun with a private beach and pool sanctuary at this family-friendly resort.
$99 nightly
$110 total
Sep 7 - Sep 8
Total with taxes and fees
Scotty's Lakeside Resort
A rectangular swimming pool with a metal ladder, surrounded by a fence and outdoor seating.
An outdoor patio with a wooden pergola, stone walls, and a fire feature.
A cozy living room with a fireplace, comfortable seating, and a large window.
A rustic bar area with a wooden counter, coffee machines, and a variety of coffee cups and mugs.

10. Super 8 by Wyndham Lake George/Downtown

Super 8 by Wyndham Lake George/Downtown
Lake George
  • Sun-splashed pool days in Lake George beckon with refreshing dips and mountain views.
$71 nightly
$79 total
Sep 22 - Sep 23
Total with taxes and fees
Super 8 by Wyndham Lake George/Downtown
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 Georgian Lakeside Resort

The Georgian Lakeside Resort

8/10 Good
"Overall the hotel was nice and the location wouldn't be beat. Amenities as far as the private beach and poolside bar/ restaurant were also great. However, the bathroom was small, and in general, the room overall was sparse re in-room amenities. One issue was some (not all) front desk staff had the personality of a stone. When checking in, I asked if it would be possible for a late (extra hour) checkout. I was told, in monotone, "We do not extend late checkouts." Fortunately, I went down early the next morning and asked the front desk manager (different person) again if we could get a late check-out; this time the response was a much more empathetic "I'm really sorry, we've got a lot of rooms booked tonight, but I can get you a half-hour extra," which was fine. One last constructive criticism - parking was tight. We were out late, and upon returning (even though we had a parking pass) all spots were taken. We were able to make our own spot - so all ended well."
John 1-night trip
Posted less than an hour ago
The Georgian Lakeside Resort
Comfort Inn & Suites Lake George

Comfort Inn & Suites Lake George

10/10 Excellent
"Comfortable and clean Great breakfast Location wonderful"
Barbara 3-night trip
Posted 2 hours ago
Comfort Inn & Suites Lake George
Lakefront Terrace Resort

Lakefront Terrace Resort

10/10 Excellent
"The view was amazing, staff was really nice very accommodating and the room was very clean."
Gabriella 3-night trip
Posted 3 hours ago
Lakefront Terrace Resort
Surfside On The Lake

Surfside On The Lake

10/10 Excellent
"Very good"
Luz Dary 1-night trip
Posted 4 hours ago
Surfside On The Lake
Holiday Inn Resort Lake George - Adirondack Area by IHG

Holiday Inn Resort Lake George - Adirondack Area by IHG

10/10 Excellent
"Rooms were very clean, staff was attentive and very friendly. Happy hour at the pool with appetizers was great!"
Raymond 2-night trip
Posted 6 hours ago
Holiday Inn Resort Lake George - Adirondack Area by IHG
The Queensbury Hotel

The Queensbury Hotel

10/10 Excellent
"There is really nothing negative I can say about The Queensbury. The room and hotel was very clean and the staff was very polite. The restaurants were busy and their staff was relaxed and very helpful. We will be returning. The only thing I missed was the chips they gave you towards breakfast."
Edward 2-night trip
Posted 1 day ago
The Queensbury Hotel
Tiki Resort

Tiki Resort

10/10 Excellent
"Excellent customer service!!"
Gail 4-night trip
Posted 1 day ago
Tiki Resort

Frequently asked questions

What are some hotels with pools in Chestertown?
Pine Tree Motel & Cabins: Provides 2 restaurants, an indoor pool, and 2 bars. Peaceful Lakeside Retreat with Private Beach: Hotel located near Great Escape. Features daily, an indoor pool, and free self parking. The Queensbury Hotel: Hotel, 10-minute walk from Fort William Henry Museum. Features a children's pool, an indoor pool, and a sauna. La Quinta Inn & Suites by Wyndham Lake George: Hotel, 1-minute walk from Lake George. Offers a private beach, a seasonal outdoor pool, and free self parking. Great Escape Lodge & Indoor Waterpark: Hotel, 1-minute walk from Lake George. Provides a private beach, a seasonal outdoor pool, and a snack bar/deli.
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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