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ChestertownUnited States of America

Top Hotels in Chestertown

Estimated price for 1 night / 2 adults
Great Oak Manor
Great Oak Manor
3.5 out of 5
10568 Cliff Rd, Chestertown, MD
The price is $159 per night

Nestled on the beach, this Chestertown bed & breakfast is next to a golf course, 9.1 mi (14.6 km) from Washington College, and 12.6 mi (20.2 km) from Rock Hall ...

4.7/5Exceptional! (22 reviews)

"Great, friendly staff; building and grounds were excellently-maintained, room was comfy."…"

Reviewed on Jan 1, 2020

Great Oak Manor
Holiday Inn Express Hotel & Suites Chestertown
Holiday Inn Express Hotel & Suites Chestertown
2.5 out of 5
150 Scheeler Road, Chestertown, MD
The price is $75 per night

Situated in Chestertown, this hotel is 0.6 mi (0.9 km) from Washington College and within 25 mi (40 km) of Rock Hall Harbor and Queenstown Premium Outlets. Queenstown ...

4.3/5Excellent! (400 reviews)

"Very pleased with our stay. Everyone was pleasant and friendly. We will make that I go to hotel in Chestertown, Md."…"

Reviewed on Mar 17, 2020

Holiday Inn Express Hotel & Suites Chestertown
Inn at Mitchell House
Inn at Mitchell House
3 out of 5
8796 Maryland Pkwy, Chestertown, MD
The price is $140 per night

Situated near the beach, this bed & breakfast is 7.2 mi (11.6 km) from Rock Hall Harbor and 11 mi (17.6 km) from Washington College.

4.8/5Exceptional! (19 reviews)
Wonderful and relaxing stay

"Lovely place, gracious owners, beautiful and spacious room, and fantastic breakfasts. I definitely want to go back! A particularly delightful place if you are a history buff, or into wildlife, as the national wildlife refuge is nearby."…"

Reviewed on Jan 12, 2020

Inn at Mitchell House

Popular places to visit in Chestertown

U.S. Naval Academy
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U.S. Naval Academy

4.5/5(446 reviews)

See where future generations of Navy and Marine Corps officers are trained at this historic federal service academy within a former fort in Annapolis harbor.

Chesapeake Bay Bridge
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Chesapeake Bay Bridge

4/5(269 reviews)

Attempt the nerve-racking drive across this long and notoriously scary bridge, which provides fabulous views of Chesapeake Bay for passengers. 

Sandy Point State Park
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Sandy Point State Park

4.5/5(13 reviews)

Sunbathe on the beach, enjoy unrivaled views of the Chesapeake Bay Bridge and go hiking, swimming, fishing and boating in this vast park. 

Fort McHenry
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Fort McHenry

4.5/5(212 reviews)

Tour the historic defense building which was the inspiration for the U.S. national anthem.

Canton Waterfront Park
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Canton Waterfront Park

Explore the great outdoors at Canton Waterfront Park, a lovely green space in Baltimore. Experience the acclaimed art scene and fascinating museums in this vibrant area.

Elk Neck State Park
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Elk Neck State Park

4.5/5(7 reviews)

Explore the great outdoors at Elk Neck State Park, a lovely green space in North East. Attend a sporting event while in this family-friendly area or simply enjoy the top-notch restaurants.

Reviews of Chestertown


Top Destination

5 - Excellent
5 - Excellent 27.586206896551722%
4 - Good
4 - Good 55.172413793103445%
3 - Okay
3 - Okay 17.24137931034483%
2 - Disappointing
2 - Disappointing 0%
1 - Terrible
1 - Terrible 0%

5/5 - Excellent


Aug 12, 2019

Chestertown is a beautiful place.

5/5 - Excellent

Verified traveler

Jul 24, 2019

None of the choices Expedia gave me for places I went to were anywhere near Chestertown. Chestertown is a very nice community with wonderful Colonial Houses, a nice harbour, interesting history, and an amazing number of great restaurants.

4/5 - Good

Verified traveler

Jun 17, 2019

Definitely the Land of Pleasant Living!

3/5 - Okay


Jun 13, 2019

We went to Washington College. Downtown Chestertown was cute.

4/5 - Good


Apr 19, 2019

Small attractive college town on the bay, good restaurants, nice period houses

5/5 - Excellent

Verified traveler

Apr 11, 2019

We were in Chestertown to visit Washington College. The town is so special and lovely! I would really love to visit when the weather is warmer to enjoy the water and all the offerings in the area.

Cities near Chestertown