Best-rated Hotels in Chestertown for an Unforgettable Stay

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We offer thousands of Chestertown hotels and accommodations from some of the world's most renowned hotel chains as well as unique gems in the region that you won’t find anywhere else.

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Hotels by class
2 stars 1
Unrated 23
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Lodges 2
Inn 1
Motel 1
Thematic Hotels
Luxury accommodations 15
Private Villas 15
Beach hotels 8
Beachfront hotels 5
Resorts 4
Pet-friendly hotels 4
Jacuzzi 3
Luxury hotels 2
Golf hotels 1
Self Catering 1

Hotels by location

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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 Popular Chestertown Hotels

9.8

Exceptional

us Phil 15 October 2022
The hotel's location was ideal and fab very close to all metro lines. Our room was new-fashioned and provided with an amazing view and extra Duvet, for instance as expected.
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9.8

Exceptional

us Glenn 09 March 2023
A flat-screen TV with cable channels, climate control and an individual safe available in the signature king suite. The bed was exceptionally comfortable and the breakfast was marvellous and nice.
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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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9.8

Exceptional

us Roger 14 January 2023
The hotel was stylish in general, had knowledgeable staff on the early morning shift. The location was easy, just 10 min walk from R Lounge. It was located in a really cool area. I appreciated functional room complete with amazing shower and 2 double beds and kettle. Everything was really good as expected, nonetheless the bathroom was leaking.
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9.8

Exceptional

us Kyle 24 February 2023
Wanted to explore New York City and this hotel was amazing base for doing it. The ideal and strategic location was a couple of blocks away from The Ride. There was a lovely restaurant just a short walk away from the venue. We had a perfectly pleasant time.
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9.8

Exceptional

us John 14 March 2023
Good for shopping. A brand-new and incredible room provided with queen beds and bathroom and skyline view. Central location, wonderful base for discovering New York City.
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9.8

Exceptional

us Paul 11 December 2022
We lovely spend 4 nights in New York City. This hotel had a central position on the main street.
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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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9.8

Exceptional

us Katherine 13 August 2022
We had a great time.
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9.8

Exceptional

us Bonnie 14 April 2023
Unbeatable spot near Broadway and Times Square and center. Also, very close to everything.
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Save Time on Trip Arrangements by Booking One of Our Hand-picked Hotels

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

963 Friends Lake Rd, Chestertown, United States

Excellent
74 reviews

247 US$

min. price/night

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

46 Fiddlehead Bay Rd, Chestertown, United States

Excellent
3 reviews

599 US$

min. price/night

Discover the hidden gems of Chestertown by booking one of its 2-star hotels.
The Lodge At Loon Lake

5381 State Route 8, Chestertown, United States

Excellent
122 reviews

159 US$

min. price/night

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