Home > Maryland > Chestertown's Top 10s > Top 10 Restaurants in Chestertown

The best Restaurants in Chestertown are:

      Rating: 5.0
Category: Restaurants
108 South Cross Street
Chestertown, Maryland 21620
(410) 778-2688
Play it Again Sam offers a fun and casual, yet sophisticated atmosphere. It is in a charming setting right near the Chester River in historic... More
      Rating: 5.0
Category: Pharmacies & Drug Stores
711 Washington Ave 26
Chestertown, Maryland 21620
(410) 778-4000
Rite Aid is convenient and has friendly floor staff. Good Pharmacy and decent prices. More
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      Rating: 4.0
Category: Bars, Pubs & Clubs
512 Washington Ave
Chestertown, Maryland 21620
(410) 778-2885
Nice b/c they have pool tables and will do pitchers. Food and drinks are affordable, and there are several pool tables so you can actually get to... More
      Rating: 4.0
Category: Hotels & Lodging
208 High St
Chestertown, Maryland 21620
(410) 778-5000
Great price for a Eastern shore hotel! Around $110 a night. Old small hotel with 11 rooms, lovingly refurbished. Staff very nice and helpful. ... More
      Rating: 4.0
Category: Restaurants
208 High St
Chestertown, Maryland 21620
(410) 778-5000
Great price for a Eastern shore hotel! Around $110 a night. Old small hotel with 11 rooms, lovingly refurbished. Staff very nice and helpful. ... More
Chestertown's Top Places
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