Hotels in Chestertown from $142 - Find Cheap Hotels with momondo

Chestertown, NY

Jul 24 — Jul 252

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Top hotels in Chestertown

Find the perfect hotel for your stay in Chestertown

Price

$86

$665

Review Score

Hotel class

Hostels and cheap hotels in Chestertown

These hotels and hostels usually make for a cheap way to stay in Chestertown

Lily Pad South At Loon Lake Near Gore Mountain

Chestertown, NY, United States

$142

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The Lodge at Loon Lake

5381 State Route 8, Chestertown, NY, United States

9.0

$233

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River Road Retreat

Chestertown, NY, United States

$171

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Homestay - Comfy Adirondack Village Home

Chestertown, NY, United States

$86

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Pine Tree Motel & Cabins

5537 State Route 8, Chestertown, NY, United States

$194

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Lily Pad North At Loon Lake Near Gore Mountain

Chestertown, NY, United States

$149

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Get the best value hotel in Chestertown

These Chestertown hotels have the best prices for their ratings

Friends Lake Inn

963 Friends Lake Road, Chestertown, NY, United States

8.6

$260

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The Fern Lodge

46 Fiddlehead Bay Road, Chestertown, NY, United States

10.0

$665

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The Lodge at Loon Lake

5381 State Route 8, Chestertown, NY, United States

9.0

$233

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Peaceful Lakeside Retreat with Private Beach

Chestertown, NY, United States

9.5

$348

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Rustic Adirondacks Home with Hot Tub and Lake Access!

Chestertown, NY, United States

9.8

$256

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Around the Mountains

Chestertown, NY, United States

9.6

$391

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momondo's favorite hotels in Chestertown

Learn more about these user-preferred hotels in Chestertown

Lily Pad North At Loon Lake Near Gore Mountain

Chestertown, NY, United States

$149

Useful insights on Chestertown hotels

Get a quick overview on price and accommodation trends for your visit in Chestertown

Lowest Hotel Price	$86
Hotels Near Airport	408

The cheapest price for a room in Chestertown found in the last 7 days is $86/night. This rate is available with Homestay - Comfy Adirondack Village Home.

There are 408 hotels in Chestertown close to Albany Intl. Baymont by Wyndham Latham Albany Airport is the nearest with a distance of 0.7 mi from this airport.

When to book a hotel in Chestertown

Check out the information below to find the best deal on a hotel room in Chestertown

What is the average price per room type in Chestertown?

The most popular room type for hotels in Chestertown is Golf, with an average price of $235/night. The second most popular room type is Luxury at $468/night, followed by Spa/Wellness at $260/night.

Information about staying in Chestertown

Read these important travel tips before booking a hotel in Chestertown

When is the best time to book a hotel in Chestertown?

September is the cheapest month to book a hotel in Chestertown. Prices can be 12% lower than other, busier months; so this is a great time to get a good deal.

Which day is cheapest to stay in Chestertown?

Hotel rooms in Chestertown are generally cheapest on Tuesday and more costly on Thursday.

How many operators does momondo search for hotels in Chestertown?

The number of operators available for hotels in Chestertown is 143 as of July 2025.

When did momondo last update prices for hotels in Chestertown?

Prices for hotels in Chestertown were last updated today.

Why use momondo?

Why should I book accomodation in Chestertown through momondo?

momondo is free to use with no hidden fees or costs. momondo searches across numerous travel websites to return hotels and accommodation options in Chestertown which you can then filter quickly and easily.

How does momondo help me find a great place to stay in Chestertown?

You can filter by price, location, amenities, review score and so much more on momondo. That is how we can help you find a great place to stay in Chestertown.