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
26 Aug - 27 Aug
Tomorrow
27 Aug - 28 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Our top choices for Chestertown hotels with a pool

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.
€97
includes taxes & fees
23 Sept - 24 Sept
The Juliana Resort

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.
€97
includes taxes & fees
27 Aug - 28 Aug
Adirondack Retreat Inn & Suites

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.
€104
includes taxes & fees
13 Sept - 14 Sept
The Georgian Lakeside Resort

4. Admiral Motel

Admiral Motel
Lake George
  • Splash into lakeside bliss at this clean motel with a seasonal outdoor pool and cosy loungers.
€74
includes taxes & fees
1 Sept - 2 Sept
Admiral Motel

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.
€93
includes taxes & fees
17 Sept - 18 Sept
Depe Dene Lakeside Resort

6. 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.
€88
includes taxes & fees
13 Sept - 14 Sept
La Quinta Inn & Suites by Wyndham Lake George

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.
€79
includes taxes & fees
3 Sept - 4 Sept
Heritage of Lake George

8. 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.
€69
includes taxes & fees
14 Sept - 15 Sept
Super 8 by Wyndham Lake George/Downtown

9. 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.
€92
includes taxes & fees
13 Sept - 14 Sept
Lakefront Terrace Resort

10. Howard Johnson by Wyndham Lake George

Howard Johnson by Wyndham Lake George
Lake George
  • Splash into holiday mode at this Lake George gem with a sun-drenched pool.
€75
includes taxes & fees
16 Sept - 17 Sept
Howard Johnson by Wyndham 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
"Great experience, will stay again."
lenny 1-night trip
Posted 1 hour ago
The Queensbury Hotel
Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites

10/10 Excellent
"Nice rooms with full kitchen. Easy parking right outside room. Great location near main area of town. Not luxurious but clean and well maintained. Reasonably priced. Friendly and helpful staff."
Neil 3-night trip
Posted 3 hours ago
Adirondack Retreat Inn & Suites
Tiki Resort

Tiki Resort

8/10 Good
"We had a great stay at Tiki Resort in Lake George! The location was perfect for everything we wanted to do, and it was especially convenient being right in the heart of Lake George. The room was clean and comfortable, and the staff were friendly and helpful throughout our stay. We also really enjoyed the pool area, which was a great bonus. It was the perfect spot for a quick getaway, and we would definitely stay here again when we’re back in Lake George. Great location, comfortable accommodations, and a fun, relaxed atmosphere!"
Carly 1-night trip
Posted 12 hours ago
Tiki Resort
Baymont by Wyndham Queensbury / Lake George

Baymont by Wyndham Queensbury / Lake George

8/10 Good
"Very good place near the highway"
René 1-night trip
Posted 12 hours ago
Baymont by Wyndham Queensbury / Lake George
The Georgian Lakeside Resort

The Georgian Lakeside Resort

10/10 Excellent
"Great location , clean and cabana bar and pool are awesome. Heated pool open late"
Mark 2-night trip
Posted 18 hours ago
The Georgian Lakeside Resort
Comfort Inn & Suites Lake George

Comfort Inn & Suites Lake George

10/10 Excellent
"Very clean, and friendly staffs."
JIMMY 2-night trip
Posted 1 day ago
Comfort Inn & Suites Lake George
Holiday Inn Resort Lake George - Adirondack Area by IHG

Holiday Inn Resort Lake George - Adirondack Area by IHG

10/10 Excellent
"."
Bob 2-night trip
Posted 2 days ago
Holiday Inn Resort Lake George - Adirondack Area by IHG
Howard Johnson by Wyndham Lake George

Howard Johnson by Wyndham Lake George

10/10 Excellent
"I had a pleasant stay at the hotel, the room and bathroom were spotless, and the staff provided outstanding customer service. While the corridors and stairs could benefit from some maintenance and the soda and ice machines could be updated, these were minor issues. overall, I would recommend this hotel to others."
Diana 1-night trip
Posted 2 days ago
Howard Johnson by Wyndham Lake George
Scotty's Lakeside Resort

Scotty's Lakeside Resort

10/10 Excellent
"Lots to do...ping pong, lake, pool, volleyball, kayak, etc."
Staci 2-night trip
Posted 4 days ago
Scotty's Lakeside 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, visit 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 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.