The 10 Best Hotels in Chestertown, MD

Fresh reviews:

What a wonderful surprise to find! We came with several friends to explore the area and were treated like royalty. Marta is not only a spectacular host but a fantastic cook as well.The rooms are well appointed with plenty of hot water and cold air (not what I am used to finding at BnB’s). The grounds are great…

Nombre O.

John L Stam House

We greatly enjoyed our stay in this comfortable and beautifully decorated Inn. Breakfasts were delicious, and the owner/hosts couldn’t have been more welcoming. The living rooms were perfect for time spent with friends (that we traveled with) and the bedrooms were lovely and comfy.

Jerry F.

Inn At Mitchell House

We had our wedding here, and the whole experience exceeded our expectations! We plan to return again for our anniversary!

Kerry K.

Brampton Bed and Breakfast Inn

Ohh the Imperial what have you done? having Sunday bloody mary brunch here during my time in college here is one of my most cherished gastronomical memories. The menu was so full of gems I would spend more time deciding than eating. The bloody mary bar was a treat with all the condiments and hot sauces you…

Jan V.

Imperial Hotel

Flies flies flies. There were flies everywhere. For me flies are an indication of a dirty establishment. Not just dirt but filth.Room size was as expected but dirty. Crumbs all over the floor and inside the pullout sofa bed.Missing smoke detectors. Holes in ceiling where previous cable TV lines were…

Sid P.

Quality Suites

Run. Do not walk. This is a horrible place. There was a wedding this weekend and most places were booked. Room was musty, no towels and bathroom was disgusting. If it wasn’t so late and we had a 2 hour drive home we wouldn’t have stayed.

Marianne W.

Driftwood Inn

15 places in Chestertown, ordered by rating:

John L Stam House

5.0

2 reviews

Telephone:	+1 410-778-1926
Address:	114 Washington Ave

Hotels / Bed & Breakfast

White Swan Tavern

5.0

1 review

Telephone:	+1 410-778-2300
Address:	228 Cannon St

Hotels / Bed & Breakfast

Inn At Mitchell House

4.8

5 reviews

Telephone:	+1 410-778-6500
Address:	8796 Maryland Pkwy

Hotels / Bed & Breakfast

Brampton Bed and Breakfast Inn

4.7

11 reviews

Telephone:	+1 410-778-1860
Address:	25227 Chestertown Rd

Bed & Breakfast / Hotels

Holiday Inn Express & Suites Chestertown

4.0

1 review

Telephone:	+1 410-778-0778
Address:	150 Scheeler Rd

Hotels / Venues & Event Spaces

Imperial Hotel

3.3

20 reviews

Telephone:	+1 410-778-5000
Address:	208 High St

Hotels /

Widow’s Walk Inn B&B

2.5

2 reviews

Telephone:	+1 410-778-6864
Address:	402 High St

Hotels / Bed & Breakfast

Quality Suites

2.6

7 reviews

Telephone:	+1 410-810-0555
Address:	160 Scheeler Rd

Hotels /

Driftwood Inn

2.2

5 reviews

Telephone:	+1 410-778-3200
Address:	609 Washington Ave

Hotels / Bed & Breakfast

Great Oak Landing Lodge & Restaurant

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Telephone:	+1 410-778-2100
Address:	22170 Great Oak Landing Rd

Hotels / Restaurants

Court Yard Inn

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Telephone:	+1 410-778-2755
Address:	6336 Church Hill Rd

Hotels /

Laurentum Inn

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Telephone:	+1 410-778-3236
Address:	954 High St

Hotels / Bed & Breakfast

Great Oak Lodge

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Telephone:	+1 410-778-5943
Address:	10568 Cliff Rd

Hotels /

Chesapeake Inns

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Telephone:	+1 410-778-4667
Address:	16090 Oakland Rd

Hotels / Bed & Breakfast

Claddaugh Farm Bed & Breakfast

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Telephone:	+1 410-778-4894
Address:	160 Claddaugh Ln

Hotels / Bed & Breakfast

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The 10 Best Hotels

Chestertown, MD, United States

Fresh reviews:

15 places in Chestertown, ordered by rating:

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