A waterfront town with a pier, dock, and several buildings.

Chestertown Hotels with Swimming Pool

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Check availability on Chestertown Hotels with Swimming Pools

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 RM470
RM522 total
includes taxes & fees
9 Nov - 10 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.
View all properties

Choose what matters most at hotels with a pool in Chestertown

Breakfast included
Hot tub

Top Chestertown Hotel Reviews

The Queensbury Hotel

The Queensbury Hotel

10/10 Excellent
"This beautiful hotel was able to handle a large wedding without encroaching on patrons unrelated to the wedding. My room was bright and well appointed. The bed affored a luxurious sleeping experience."
John J 1-night trip
Posted 1 day ago
The Queensbury Hotel
Fort William Henry Hotel and Conference Center

Fort William Henry Hotel and Conference Center

10/10 Excellent
"Loved the views and firepits!"
John 4-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 sunloungers, a pool and complimentary wireless Internet access. Great Escape Lodge & Indoor Waterpark: Hotel located near Great Escape. Features buffet, an indoor pool and free self parking. 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. The Georgian Lakeside Resort: Features 2 restaurants, an indoor pool and 2 bars. The Queensbury Hotel: 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, visit 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 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.

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