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

This weekend
6 Nov - 8 Nov
Next weekend
13 Nov - 15 Nov

Our top choices for Chestertown hotels with a pool

Room

1. Friends Lake Inn

Friends Lake Inn
4.0 star property
Chestertown
8.6 out of 10, Excellent, (137 reviews)
"Great breakfast, very friendly staff and beautiful place"
United States
Pierre
The price is AED 426
AED 473 total
includes taxes & fees
8 Nov - 9 Nov
Friends Lake Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at hotels with a pool in Chestertown

Breakfast included
Hot tub

Top Chestertown Hotel Reviews

Fort William Henry Hotel and Conference Center

Fort William Henry Hotel and Conference Center

10/10 Excellent
"Great location"
Cynthia 1-night trip
Posted 2 days ago
Fort William Henry Hotel and Conference Center

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.