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 towns 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 dozen 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 heritage there are several self-guided walking tours, driving tours, river excursion 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.

Browse Our Cambridge Vacation Rentals Below

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Belle Aire Landing FROM $11900

Belle Aire Landing

East New Market
Beds: 9 | Baths: 6 | Sleeps: 22
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Tidal Serenity FROM $2850

Tidal Serenity

Taylors Island
Beds: 5 | Baths: 2.5 | Sleeps: 15
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Bayberry Cove FROM $7000

Bayberry Cove

Cambridge
Beds: 7 | Baths: 5.5 | Sleeps: 17
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Hudson Manor FROM $6500

Hudson Manor

Cambridge
Beds: 7 | Baths: 6 | Sleeps: 22
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Holland Point Preserve FROM $4165

Holland Point Preserve

Taylors Island
Beds: 5 | Baths: 5 | Sleeps: 14
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Willoughby FROM $5250 - $7750

Willoughby

Cambridge
Beds: 7 | Baths: 6 | Sleeps: 24
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Indian Fields FROM $3500

Indian Fields

Cambridge
Beds: 5 | Baths: 4.5 | Sleeps: 13
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Bay Water Cottage FROM $2135

Bay Water Cottage

Church Creek
Beds: 4 | Baths: 3.5 | Sleeps: 8
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