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

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.
¥16,255
¥18,043 total
includes taxes & fees
Sep 23 - Sep 24
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.
¥14,309
¥16,454 total
includes taxes & fees
Aug 31 - Sep 1
Adirondack Retreat Inn & Suites

3. Admiral Motel

Admiral Motel
Lake George
  • Splash into lakeside bliss at this clean motel with a seasonal outdoor pool and cozy loungers.
¥12,478
¥13,850 total
includes taxes & fees
Sep 1 - Sep 2
Admiral Motel

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.
¥17,370
¥19,281 total
includes taxes & fees
Sep 13 - Sep 14
The Georgian Lakeside Resort

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.
¥15,633
¥17,351 total
includes taxes & fees
Sep 17 - Sep 18
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.
¥13,741
¥15,251 total
includes taxes & fees
Sep 16 - Sep 17
Lakefront Terrace Resort

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.
¥13,195
¥14,647 total
includes taxes & fees
Sep 17 - Sep 18
Heritage of Lake George

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.
¥22,079
¥30,171 total
includes taxes & fees
Sep 23 - Sep 24
Lodge at Schroon Lake

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.
¥15,777
¥17,512 total
includes taxes & fees
Sep 8 - Sep 9
Scotty's Lakeside Resort

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.
¥11,219
¥12,770 total
includes taxes & fees
Sep 14 - Sep 15
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

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

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

8/10 Good
"Some bacon and berries would be nice. Beds could be replaced."
Kathy 4-night trip
Posted 1 hour ago
Country Inn & Suites by Radisson, Lake George (Queensbury), NY
Comfort Inn & Suites Lake George

Comfort Inn & Suites Lake George

10/10 Excellent
"Nice quiet hotel with friendly staff."
Justin 1-night trip
Posted 1 hour ago
Comfort Inn & Suites Lake George
Great Escape Lodge & Indoor Waterpark

Great Escape Lodge & Indoor Waterpark

10/10 Excellent
"Very cool weekend escape with the kids."
Ana Maria 2-night trip
Posted 12 hours ago
Great Escape Lodge & Indoor Waterpark
Tiki Resort

Tiki Resort

10/10 Excellent
"My wife and kids had an amazing time at the Tiki Resort. Room was spacious, clean and updated. Staff was friendly, and the make to order breakfast was great. In close proximity to downtown , very private and kids enjoyed both pools. Would definitely stay again"
Dillon 3-night trip
Posted 12 hours ago
Tiki Resort
The Georgian Lakeside Resort

The Georgian Lakeside Resort

10/10 Excellent
"Room was clean bar was great and restaurant we ate breakfast there and order appetizers at pool bar.nice place beach pool and bar on property.Also can walk to town Seen fireworks show right from bar"
Eva 3-night trip
Posted 14 hours ago
The Georgian Lakeside Resort
Baymont by Wyndham Queensbury / Lake George

Baymont by Wyndham Queensbury / Lake George

10/10 Excellent
"N/A"
Matthew 4-night trip
Posted 15 hours ago
Baymont by Wyndham Queensbury / Lake George
Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites

8/10 Good
"Check in was a breeze. We had a room with a jacuzzi tub. One must realize that this property as well as most of the lakeside motels are old. The room had knotty pine walls and big beams. Great old fashioned vibe. There was a nice closet and some built in drawers as well as a dresser. The room was very clean and the bathroom clean as well. The jacuzzi worked great. This is a larger property with multiple buildings. Motel style, you can park right in front of your room. Our building was nearest to the swimming pool which is enclosed in a glass structure. We were in there for hours. The location is at the North end of the strip and a short walk to the shops and restaurants. We enjoyed our stay and have zero complaints."
John C. 2-night trip
Posted 16 hours ago
Adirondack Retreat Inn & Suites
The Queensbury Hotel

The Queensbury Hotel

8/10 Good
"The only problem was that the WiFi service was spotty."
Diane 2-night trip
Posted 17 hours ago
The Queensbury Hotel
Howard Johnson by Wyndham Lake George

Howard Johnson by Wyndham Lake George

8/10 Good
"Comfortable bed with great pillows! Clean room! Great location! Only hitch, not enough hooks in bathroom."
VIADEL 3-night trip
Posted 2 days ago
Howard Johnson by Wyndham Lake George

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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