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
2 stars 2
Unrated 5
Thematic Hotels
Pet-friendly hotels 5
Historical hotels 3
Luxury accommodations 3
Vacation Rentals 2
Hotels with indoor pool 2
Extended Stay 2
Resorts 1
Boutique hotels 1
Golf hotels 1
Beach hotels 1
Business hotels 1

Hotels by location

Nearby
Kent Plaza Shopping Center 9
Washington College Chestertown 9
Kent County Arts Council Inc 9
Imagination Alley 9
Landmarks
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Popular attractions

Welcome to Chestertown

Chestertown, nestled on the banks of the Chester River, offers an enchanting blend of rich colonial history, scenic beauty, and vibrant cultural experiences. Immerse yourself in the town's picturesque streets lined with stunning 18th-century homes, explore its charming boutiques and art galleries, and savor the local culinary delights. Discover the warmth of this inviting community, and let Chestertown captivate you with its incredible charm. Embark on an unforgettable journey to Chestertown and experience its magic firsthand.

What our users say about Chestertown hotels

9.8

Exceptional

us Steve 13 January 2023
The room was updated and had a nice view of the water. Having wake-up service was a cool amenity. - the staff was accommodating and exceptional.
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9.8

Exceptional

us Alice 01 September 2022
This place is quite clean with a very good staff and a convenient location.
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9.8

Exceptional

us Bob 19 March 2023
This venue has a great location near the waterfront and harbor, and the staff were friendly and helpful throughout our stay.
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9.8

Exceptional

us J. 21 June 2022
It has amicable, genuinely helpful staff.
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9.8

Exceptional

us Patricia 16 November 2022
The rooms were spacious and had comfortable beds, the staff was exceptional, and my stay here was really comfortable and enjoyable.
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9.8

Exceptional

us Mark 16 July 2022
The hotel was wonderful with amiable staff members. Brand-new and spotless room available with a classy bathroom and the fridge. Accommodating staff, excellent stay. Comfy and best possible spot near to harbor, Gaylord convention center, Tanger Outlets.
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9.8

Exceptional

us Peter 28 September 2021
I had very pleasant days staying at this family-run hotel.
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9.8

Exceptional

us Pat 06 May 2022
Liked this hotel, had 3 fun filled days here. Well-equipped and brand-new rooms, pleasant views to a room with a nice interior view.
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9.8

Exceptional

us Alan 21 July 2022
The room had a modern vibe with a TV and 2 double beds, for instance. It was easy to get to the car rental spot and to Baltimore from here. 🚗
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9.8

Exceptional

us Michael 15 September 2022
The room was amazing, and the balcony was a great spot to relax.
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Save time on your trip arrangements by booking one of our hand-picked hotels

Top 5-star hotels
Exclusive 3-star hotels
Quality 2-star hotels
Indulge yourself with luxury and comfort as you explore the exciting attractions of Chestertown.
Brampton 1860 Bed & Breakfast

25227 Chestertown Road, Chestertown, United States

Excellent
14 reviews

330 US$

min. price/night

Enjoy truly authentic experiences without compromising comfort and convenience.
Inn At Mitchell House

8796 Maryland Pkwy, Chestertown, United States

Quality Suites

160 Scheeler Rd., Chestertown, United States

75 US$

min. price/night

Discover the hidden gems of Chestertown by booking one of its budget-friendly hotels.
Comfort Inn & Suites Chestertown

150 Scheeler Road, Chestertown, United States

Good
239 reviews

92 US$

min. price/night

Driftwood Inn

609 Washington Avenue, Chestertown, United States

Average
70 reviews

57 US$

min. price/night

Travelers’ choice

Check out the most booked accommodations to find reliable places that our users have tried and tested.
Lodging At The Imperial Hotel

208 High Street, Chestertown, United States

194 US$

min. price/night

Luxury 4 Bedroom Vacation Home Downtown Chestertown - Sleeps 11

114 High Street, Chestertown, United States

Pet-Friendly Home On Chester River With Dock!

205 Fey Rd, Chestertown, United States

793 US$

min. price/night

Walk To Historic Chestertown Dog-Friendly Retreat

709 High St, Chestertown, United States

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