Title: Book the Best Hotels with POOL in Chestertown in 2025 | Expedia.ca

  

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# Find Hotels with a Pool in Chestertown, NY from CA $344

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## Check availability on Chestertown Hotels with a Pool

Tonight

[Sep 24 - Sep 25](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-09-24&endDate=2025-09-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Sep 25 - Sep 26](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-09-25&endDate=2025-09-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-09-26&endDate=2025-09-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-10-03&endDate=2025-10-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Chestertown Hotels with a Pool

## Our top choices for Chestertown hotels with a pool

![Premier Room](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/8bdcc127.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premier Room](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/65af6a05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/0a784cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast and dinner served, American cuisine](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/1b13c3a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Friends Lake Inn

Chestertown

8.8/10

Excellent

(101)

"Staff was great. The inn is unique. Perfect!"

CA $310

CA $344 total

includes taxes & fees

Sep 26 - Sep 27

[](https://www.expedia.ca/Lake-George-Hotels-Friends-Lake-Inn.h9675030.Hotel-Information)

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](https://expedia.ca/Hotel-Search?startDate=2025-10-09&endDate=2025-10-10&regionId=89045&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true)

## Top Chestertown Hotel Reviews

![The Queensbury Hotel](//images.trvl-media.com/lodging/1000000/50000/40400/40334/c38b9040_y.jpg)

### The Queensbury Hotel

10/10 Excellent

"I liked everything about the queensbury "

[](https://expedia.ca/Lake-George-Hotels-The-Queensbury-Hotel.h40334.Hotel-Information)

![The Georgian Lakeside Resort](//images.trvl-media.com/lodging/2000000/1200000/1194100/1194009/f69be4ef_y.jpg)

### The Georgian Lakeside Resort

10/10 Excellent

"Perfect space for a long weekend! Love the bar happy hour and cabana. Lake was cold but pool was heated! Loved everything. second time staying and we will book for next year too!! Walkable to everything too!!"

[](https://expedia.ca/Lake-George-Hotels-The-Georgian-Lakeside-Resort.h1194009.Hotel-Information)

![Holiday Inn Resort Lake George - Adirondack Area by IHG](//images.trvl-media.com/lodging/1000000/10000/1200/1178/3f808d49_y.jpg)

### Holiday Inn Resort Lake George - Adirondack Area by IHG

10/10 Excellent

"We just loved the hot tub and swimming pool. The breakfast was delicious and the staff was very helpful when needed. A beautiful setting. "

[](https://expedia.ca/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.Hotel-Information)

![Lakefront Terrace Resort](//images.trvl-media.com/lodging/1000000/900000/899000/898952/7471e44f_y.jpg)

### Lakefront Terrace Resort

10/10 Excellent

"Friendly personal "

[](https://expedia.ca/Lake-George-Hotels-Lakefront-Terrace-Resort.h898952.Hotel-Information)

![Courtyard by Marriott Lake George](//images.trvl-media.com/lodging/16000000/15200000/15191100/15191022/f47df569_y.jpg)

### Courtyard by Marriott Lake George

10/10 Excellent

"Great views "

[](https://expedia.ca/Lake-George-Hotels-Courtyard-By-Marriott-Lake-George.h15191022.Hotel-Information)

![Comfort Inn & Suites Lake George](//images.trvl-media.com/lodging/2000000/1650000/1640200/1640103/93d3500a_y.jpg)

### Comfort Inn & Suites Lake George

10/10 Excellent

"Good "

[](https://expedia.ca/Lake-George-Hotels-Comfort-Inn-Suites.h1640103.Hotel-Information)

![Fort William Henry Hotel and Conference Center](//images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/a8530560_y.jpg)

### Fort William Henry Hotel and Conference Center

10/10 Excellent

"Outdated but otherwise great!"

[](https://expedia.ca/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.Hotel-Information)

![Tiki Resort](//images.trvl-media.com/lodging/1000000/50000/43200/43183/5068bb33_y.jpg)

### Tiki Resort

10/10 Excellent

"Absolutely gorgeous hotel. The entire resort was spotless. All the staff were genuinely friendly and helpful. Couldn't have asked for a better stay. Can't wait to return."

[](https://expedia.ca/Lake-George-Hotels-Tiki-Resort.h43183.Hotel-Information)

![Baymont by Wyndham Queensbury / Lake George](//images.trvl-media.com/lodging/1000000/30000/23700/23630/cf943129_y.jpg)

### Baymont by Wyndham Queensbury / Lake George

10/10 Excellent

"Good"

[](https://expedia.ca/Lake-George-Hotels-Baymont-By-Wyndham-Queensbury-Lake-George.h23630.Hotel-Information)

## Frequently asked questions

### What are some hotels with pools in Chestertown?

> [Pine Tree Motel & Cabins](https://www.expedia.ca/Lake-George-Hotels-Pine-Tree-Motel-Cabins.h8355292.Hotel-Information): Provides 2 restaurants, an indoor pool, and 2 bars. [Friends Lake Inn](https://www.expedia.ca/Lake-George-Hotels-Friends-Lake-Inn.h9675030.Hotel-Information): Hotel, 1-minute walk from Lake George. Offers a private beach, a seasonal outdoor pool, and a snack bar/deli. [The Queensbury Hotel](https://www.expedia.ca/Lake-George-Hotels-The-Queensbury-Hotel.h40334.Hotel-Information): Hotel, 1-minute walk from Lake George. Features a private beach, a seasonal outdoor pool, and free self parking. [Six Flags Great Escape Lodge & Indoor Waterpark](https://www.expedia.ca/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.Hotel-Information): Hotel located near Six Flags Great Escape. Offers daily, an indoor pool, and free self parking. [Lakefront Terrace Resort](https://www.expedia.ca/Lake-George-Hotels-Lakefront-Terrace-Resort.h898952.Hotel-Information): Hotel, 8-minute walk from Six Flags Great Escape. Provides a seasonal outdoor pool, an indoor pool, and daily.

### 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.

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-   [Castles in The Glen](https://www.expedia.ca/The-Glen-Castles.d553248635975850312-aaCastles.Travel-Guide-Accommodation)
-   [Chalets in The Glen](https://www.expedia.ca/The-Glen-Chalets.d553248635975850312-aaChalets.Travel-Guide-Accommodation)
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-   [The Glen Hotels](https://www.expedia.ca/The-Glen-Hotels.d553248635975850312.Travel-Guide-Hotels)
-   [Inns in The Glen](https://www.expedia.ca/The-Glen-Inns.d553248635975850312-aaInns.Travel-Guide-Accommodation)
-   [Lodges in The Glen](https://www.expedia.ca/The-Glen-Lodges.d553248635975850312-aaLodges.Travel-Guide-Accommodation)
-   [Resorts in The Glen](https://www.expedia.ca/The-Glen-Resort-Hotels.d553248635975850312-aaResortHotels.Travel-Guide-Accommodation)
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-   [Hotels with Balconies in Upstate New York](https://www.expedia.ca/Upstate-New-York-Hotels-Hotels-With-Balconies.0-0-d6234083-tHotelswithBalconies.Travel-Guide-Filter-Hotels)
-   [Hotels with Bar in Upstate New York](https://www.expedia.ca/Upstate-New-York-Hotels-Hotels-With-Bar.0-0-d6234083-tHotelswithBar.Travel-Guide-Filter-Hotels)
-   [Hotels with Free Airport Shuttle in Upstate New York](https://www.expedia.ca/Upstate-New-York-Hotels-Hotels-With-Free-Airport-Shuttle.0-0-d6234083-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels)
-   [Hotels with Free Parking in Upstate New York](https://www.expedia.ca/Upstate-New-York-Hotels-Hotels-With-Free-Parking.0-0-d6234083-tHotelswithFreeParking.Travel-Guide-Filter-Hotels)
-   [Hotels with smoking rooms in Upstate New York](https://www.expedia.ca/Upstate-New-York-Hotels-Hotels-With-Smoking-Rooms.0-0-d6234083-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels)

-   [Flights to Pottersville](https://www.expedia.ca/Cheap-Flights-To-Pottersville.d6349845.Travel-Guide-Flights)
-   [Flights from Brant Lake](https://www.expedia.ca/lp/flights/6347839/flights-from-brant-lake)

-   [Loon Lake Beach](https://www.expedia.ca/Loon-Lake-Beach-Chestertown.d553248621554184980.Vacation-Attraction)

-   [Car rental Pottersville](https://www.expedia.ca/Car-Rentals-In-Pottersville.d6349845.Car-Rental-Guide)

-   [Book Hotels with a Pool in Chestertown on Expedia.com](https://www.expedia.com/Chestertown-Hotels-Hotel-With-Pool.0-0-d89045-tHotelwithPool.Travel-Guide-Filter-Hotels)