Cambridge

Shopping Boutique Shopping in Historic District
Restaurants Several within minutes
Golf Course River Marsh Golf Course
Groceries Several Major and Gourmet Stores

Community Information


One of the oldest towns in Maryland, this small town sits on the banks of the Choptank River. About an hour from the Chesapeake Bay Bridge, Dorchester County boasts famous residents such as Harriet Tubman, the most famous of Underground Railroad "conductors" who led dozens of enslaved people to freedom, and Sharpshooter Annie Oakley. Also, more Maryland governors are from this area than any other with the exception of Baltimore City! Explore Cambridge and surrounding Dorchester County's long history as an agricultural and canning powerhouse, and their boatbuilding and maritime heritagethere are several self-guided walking tours, driving tours, river excursions and museums to help you experience the stories and history. Called the "Heart of Chesapeake Country" because of it's location and shape, there are 1700 miles of shoreline surrounding 39 percent of Maryland's wetlands in the area, providing endless opportunities for kayaking, biking, and exploring.
There are several great restaurants to try and they range from fresh local seafood to eclectic bistros--- Bistro Poplar(traditional French cuisine), Leaky Petes Oyster and Wine Bar (Casual dining with raw bar, steamed shrimp, mussels, and clams, plus sandwiches) , Jimmy & Sook's Raw Bar and Grill (classic Eastern Shore recipes with a modern flare), High Spot (Gastropub, specializing in high-quality fresh cuisine), Blue Point Provision Company (the Hyatt Regency's with traditional Eastern Shore seafood), and Snappers Waterfront Cafe and Portside (great places to soak in the local flavor) The downtown features locally owned independent shops featuring jewelry, unique boutiques, stores selling handmade treasures from local artisans, and art galleries. A few of our favorites are Dragonfly, Sunnyside and Bliss Jewelry. Major area events include the Cambridge Classic Powerboat Regatta in July, the Seafood Fest-I-Val in August, the Chesapeake Heritage Skipjack Race in September and the Eagleman Race in June.

Community Vacation Homes


Starting at (USD)

$360.00

Dorchester County
  • 8 Guests
  • 4 Bedrooms
  • 3.5 Baths
  • Code: Bay Water Cottage
View Rental
Starting at (USD)

$650.00

Dorchester County
  • 13 Guests
  • 5 Bedrooms
  • 4.5 Baths
  • Code: Indian Fields
  • Pets Allowed
View Rental
Starting at (USD)

$665.00

Dorchester County
  • 14 Guests
  • 5 Bedrooms
  • 5 Baths
  • Code: Holland Point Preserve
  • Pets Allowed
View Rental
Starting at (USD)

$1,300.00

Dorchester County
  • 22 Guests
  • 7 Bedrooms
  • 6 Baths
  • Code: Hudson Manor
  • Pets Allowed
View Rental