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

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Check availability on Chestertown Cheap Hotels

Tonight
Aug 21 - Aug 22
Tomorrow
Aug 22 - Aug 23
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

Our top choices for Chestertown cheap hotels

1. Friends Lake Inn

Friends Lake Inn
Chestertown
United States
Jonathan
NT$4,724
NT$5,244 total
includes taxes & fees
Sep 21 - Sep 22
Friends Lake Inn

2. Pine Tree Motel & Cabins

Pine Tree Motel & Cabins
Chestertown
United States
Andrew
NT$5,589
NT$6,204 total
includes taxes & fees
Aug 23 - Aug 24
Pine Tree Motel & Cabins

3. The Fern Lodge

The Fern Lodge
Chestertown
United States
robert
NT$12,812
NT$14,221 total
includes taxes & fees
Aug 23 - Aug 24
The Fern Lodge

4. Super 8 by Wyndham Lake George/Warrensburg Area

Super 8 by Wyndham Lake George/Warrensburg Area
Lake George
United States
eric
NT$2,282
NT$2,532 total
includes taxes & fees
Sep 8 - Sep 9
Super 8 by Wyndham Lake George/Warrensburg Area

5. The Alpine Lodge

The Alpine Lodge
North Creek
United States
Michael
NT$3,465
NT$4,188 total
includes taxes & fees
Aug 27 - Aug 28
The Alpine Lodge

6. The Juliana Resort

The Juliana Resort
Diamond Point
United States
Jozefina
NT$3,481
NT$3,864 total
includes taxes & fees
Sep 21 - Sep 22
The Juliana Resort

7. Lodge at Schroon Lake

Lodge at Schroon Lake
Schroon Lake
United States
Helen
NT$4,425
NT$6,047 total
includes taxes & fees
Sep 20 - Sep 21
Lodge at Schroon Lake

8. Admiral Motel

Admiral Motel
Lake George
United States
Avin
NT$2,501
NT$2,776 total
includes taxes & fees
Sep 7 - Sep 8
Admiral Motel

9. Howard Johnson by Wyndham Lake George

Howard Johnson by Wyndham Lake George
Lake George
United States
Brian
NT$2,523
NT$2,801 total
includes taxes & fees
Sep 20 - Sep 21
Howard Johnson by Wyndham Lake George

10. Maple Leaf Motel

Maple Leaf Motel
Schroon Lake
United States
Angelo
NT$3,708
NT$4,190 total
includes taxes & fees
Aug 24 - Aug 25
Maple Leaf Motel
View all properties

Top Chestertown Hotel Reviews

Comfort Inn & Suites Lake George

Comfort Inn & Suites Lake George

10/10 Excellent
"Great"
Patrick 1-night trip
Posted less than an hour ago
Comfort Inn & Suites Lake George
Tiki Resort

Tiki Resort

8/10 Good
"Room was well kept and spacious. Outside of property could use some attention. Laurie in the bar was awesome. We would stay again"
Elizabeth 2-night trip
Posted 12 hours ago
Tiki Resort
Howard Johnson by Wyndham Lake George

Howard Johnson by Wyndham Lake George

10/10 Excellent
"You stay here every year . Great motel and close to everything . Walking distancing"
Jeffrey 3-night trip
Posted 14 hours ago
Howard Johnson by Wyndham Lake George
Baymont by Wyndham Queensbury / Lake George

Baymont by Wyndham Queensbury / Lake George

10/10 Excellent
"Breakfast was not good since not enough food and choice also coffee was very bad"
Kooran 3-night trip
Posted 17 hours ago
Baymont by Wyndham Queensbury / Lake George
The Georgian Lakeside Resort

The Georgian Lakeside Resort

10/10 Excellent
"We had a wonderful stay at the hotel and truly enjoyed every part of it! The location was absolutely perfect, and the views were beautiful. We especially loved the pool — it was a great place to relax and enjoy our time. The food was also delicious, and everything was well prepared. Overall, the hotel had a great atmosphere, beautiful surroundings, and everything we needed for a relaxing getaway. We really enjoyed our stay and would definitely recommend this hotel to others. We would love to come back again! ❤️"
Danara 3-night trip
Posted 17 hours ago
The Georgian Lakeside Resort
Lakefront Terrace Resort

Lakefront Terrace Resort

10/10 Excellent
"Absolutely Amazing Stay! ⭐⭐⭐⭐⭐ We had such a wonderful stay at this motel! The place is absolutely beautiful, peaceful, and very clean. The view was breathtaking and honestly one of the best parts of our stay — we could have sat there for hours just enjoying the scenery! 😍 The swimming pool was also extremely clean and well maintained, which made it even more enjoyable, especially for the kids. Everything was neat, comfortable, and welcoming. The whole property has such a relaxing atmosphere, and you can really tell that they care about keeping the place nice for their guests. We had a fantastic experience and would definitely recommend this motel to anyone looking for a beautiful, clean, and relaxing place to stay. We would absolutely come back again! ❤️"
Nor 3-night trip
Posted 19 hours ago
Lakefront Terrace Resort

Frequently asked questions

What is Chestertown like for travelers on a budget?
Chestertown offers cheap accommodation options and a variety of places to visit, making it a great getaway spot for budget travelers. You can find ways to save money while getting to know this destination, which is home to attractions like Friends Lake, Loon Lake, and Hudson River.
When is the best time for a budget trip to Chestertown?
Weather is probably a major factor when you plan your trip to Chestertown, and keep in mind that cheaper options are usually available when the weather isn't as good. 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.
What is there to see and do in Chestertown?
Chestertown is known for its lake views and offers things to see and do without spending a fortune. You can budget for the local attractions that interest you most, and then fill your itinerary with activities that cost little or nothing at all. Enjoy the outdoors at Friends Lake and Loon Lake, or check out the area's cultural spots like The Sembrich.
How can I get to Chestertown and get around on a budget?
Scoping out the transportation options in Chestertown is a smart way to keep your trip affordable. The closest airport is Glens Falls, NY (GFL-Floyd Bennett Memorial), situated 23.6 mi (38 km) away. Chestertown might not have very many public transportation choices so a car rental could be an economical alternative to see more of the area.

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