Best-rated hotels in Chestertown for your unforgettable stay

Detailed descriptions, travelers’ reviews, and handpicked hotel collections will help you book your perfect accommodation.

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Why book with us?

Choose from exclusive hotel collection

We offer thousands of Chestertown hotels and accommodations from world's renowned hotel chains to unique gems of the region you won’t find anywhere else.

Enjoy seamless booking experience

Once you choose your best place to stay, take a minute to complete a quick reservation form and get an instant confirmation letter to your email address.

Benefit from flexible travel options

We provide the most flexible cancellation options, so you get your deposit back in case of a change of plans or other unforeseen circumstances.

Find a hotel

Hotels by class
5 stars 1
4 stars 1
2 stars 2
Unrated 31
Accommodation type
Holiday homes 26
Apartments 3
Chalet 1
Farm stay 1
Motel 1
Hotel 1
Bed & Breakfast 1
Inn 1
Thematic Hotels
Vacation Rentals 30
Extended Stay 30
Luxury accommodations 13
Private Villas 12
Cheap and budget hotels 9
Beach hotels 9
Pet-friendly hotels 7
Beachfront hotels 7
Family Friendly hotels 4
Jacuzzi 3
Resorts 2
Central hotels 1
Luxury hotels 1
All Chestertown hotels

Hotels by location

Nearby
City Center Chestertown 12
Dynamite Hill Tow 9
Dynamite Hill - Chestertown 9
Landmarks
Landmark
Popular attractions
New York State >
Chestertown

Welcome to Chestertown

Nestled on the banks of the scenic Chester River, Chestertown invites you to explore its rich history and charming small-town vibe. With its well-preserved colonial architecture, vibrant arts scene, and numerous outdoor activities, there's something for everyone. Whether you're strolling along the brick sidewalks of historic downtown, savoring local cuisine, or immersing yourself in the town's lively festivals, Chestertown promises an unforgettable experience. Discover the hidden gems of this delightful town and begin your journey to Chestertown today!

What our users say about Chestertown hotels

Doubletree By Hilton New York Times Square West
9.8

Exceptional

us Phil 15 October 2022
The location of this place is perfect, very close to all metro lines, and our room had a modern design with a fantastic view and an extra duvet provided.
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Hotel Edison Times Square
9.8

Exceptional

us Glenn 09 March 2023
In the signature king suite, you can enjoy watching TV on a flat-screen with lots of channels, control the room temperature to your liking, and keep your valuables safe in an individual safe. The bed was super comfy, making for a great night's sleep. Plus, the breakfast here was simply amazing and really delicious! 🍳
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Seneca Niagara Resort & Casino (Adults Only)
9.8

Exceptional

us Randall 14 December 2022
Our room was a king suite with all the amenities we needed, including climate control, pay TV, and coffee/tea making equipment. The location of this venue was fantastic, with a beautiful water fountain nearby and easy accessibility. we had a wonderful experience here and would highly recommend it.
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Moxy Nyc Times Square
9.8

Exceptional

us Roger 14 January 2023
The hotel was stylish and located in a really cool area. the staff on the early morning shift were knowledgeable. - the location was convenient, just a 10-minute walk from R Lounge. - I loved the functional room with an amazing shower, 2 double beds, and a kettle.
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Hyatt Place New York City - Times Square
9.8

Exceptional

us Kyle 24 February 2023
the hotel was an amazing base for exploring New York City. the ideal location was just a couple of blocks away from the Ride. 3. There was a lovely restaurant within a short walk from the hotel venue.
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Millennium Hotel Broadway Times Square
9.8

Exceptional

us John 14 March 2023
A great spot for shopping with a fantastic new room featuring queen beds, a bathroom, and a view of the skyline, in a central location to explore the city.
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New Yorker By Lotte Hotels
9.8

Exceptional

us Paul 11 December 2022
Stayed at this hotel for 4 nights. The location was great, right on the main street. 🏙️
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Row Nyc At Times Square
9.8

Exceptional

us Betty 14 September 2022
Great location near Palace Theatre! The area around here is super fun, with Times Square, restaurants, and the subway all within easy reach. It's a really convenient spot to be based out of. 🎉
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Riu Plaza New York Times Square
9.8

Exceptional

us Katherine 13 August 2022
We had a great time.
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The Manhattan At Times Square
9.8

Exceptional

us Bonnie 14 April 2023
Great location right near Broadway and Times Square, can't beat that! Also, super close to everything around here. 🌟
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Save time on your trip arrangements by booking one of our hand-picked hotels

Top 5-star hotels
Best 4-star hotels
Quality 2-star hotels
Indulge yourself with luxury and comfort as you explore the exciting attractions of Chestertown.
Friends Lake Inn

963 Friends Lake Rd, Chestertown, United States

Good
45 reviews

232 US$

min. price/night

Experience the best value for your money by checking out our selection of 4-star Chestertown hotels.
The Fern Lodge

46 Fiddlehead Bay Rd., Chestertown, United States

Excellent
2 reviews

665 US$

min. price/night

Discover the hidden gems of Chestertown by booking one of its budget-friendly hotels.
The Lodge At Loon Lake

5381 State Route 8, Chestertown, United States

Excellent
94 reviews

159 US$

min. price/night

Pine Tree Motel & Cabins

5537 State Route 8, Chestertown, United States

Excellent
1 review

Travelers’ choice

Check out the most booked accommodations to find reliable places that our users have tried and tested.
Rustic Adirondacks Home With Hot Tub And Lake Access!

7133 U.S. 9, Chestertown, United States

Excellent
4 reviews

471 US$

min. price/night

Big Bear Lodge With Sauna

5056 State Route 8, Chestertown, United States

Excellent
4 reviews

Pine'S Way Camp Villa

Chestertown, United States

Excellent
4 reviews

592 US$

min. price/night

Around The Mountains Villa

89 Mountain Path, Chestertown, United States

Excellent
4 reviews

565 US$

min. price/night

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