A historic white mansion with a sign in front.

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November 2026

December 2026

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Charming coastal towns and pristine beaches dot the Chesapeake Bay's eastern shoreline, inviting you to explore maritime history and savour fresh seafood. Kayak through serene marshlands, visit Assateague Island's wild ponies, or take a scenic drive to discover quaint antique shops and waterfront restaurants.

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Budget Hotels in Annapolis
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Annapolis Hotels
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B&B in Anne Arundel County
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Cottages in Anne Arundel County
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Motels in Anne Arundel County
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Arnold Hotels
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Cabin Rentals in Baltimore County
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Cottages in Calvert County
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Cottages in Charles County
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Hotels near Coco's Funhouse
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Cordova Hotels
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Crofton Hotels
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Beach Resorts in Calvert County
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Beach Resorts in Maryland
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Budget Hotels in Maryland
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Hotels with smoking rooms in Maryland
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Maryland Hotels
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Dundalk Hotels
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Easton Hotels
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Glen Burnie Hotels
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Red Roof Inn Hotels in Kent Island
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Apartments in Laurel
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Millersville Hotels
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Aparthotels in Mount Rainier
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Gay friendly Hotels in Murray Hill
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Pasadena Hotels
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Delta Hotels in Point Pleasant
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Preston Hotels
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Apartments in Prince George's County
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Cabin Rentals in Prince George's County
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Motels in Prince George's County
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Riviera Beach Hotels
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Rose Haven Hotels
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Hotels with smoking rooms in Salisbury
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Solomons Hotels
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Cottages in St. Mary's County
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St. Michaels Hotels
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Stevensville Hotels
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Budget Hotels in Upper Marlboro
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Hotels with indoor pool in Upper Marlboro
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Upper Marlboro Hotels
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Wingate Hotels
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Flights to Maryland
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Flights to Annapolis
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Flights to Marydel
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Flights to Prince Frederick
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Flights to Sunderland
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Flights to Trappe
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Flights to Upper Marlboro
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Flights from Lee
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Flights from Maryland
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Flights from Bowie
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Flights from Pittsburgh (AGC) to Easton (ESN)
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Flights from Alpena (APN) to Baltimore (BWI)
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Flights from Beaver Falls (BFP) to Camp Springs (ADW)
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Flights from Nashville (BNA) to Easton (ESN)
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Flights from Baltimore (BWI) to Annapolis (ANP)
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Flights from Dublin (DUB) to Baltimore (BWI)
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Flights from Georgetown (GEO) to Baltimore (MTN)
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Flights from Laughlin (IFP) to Salisbury (SBY)
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Flights from Manta (MEC) to Easton (ESN)
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Flights from Manila (MNL) to Salisbury (SBY)
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Flights from Chicago (ORD) to Salisbury (SBY)
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Flights from Paris (PAR) to Annapolis (ANP)
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Flights from Plattsburgh (PBG) to Salisbury (SBY)
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Flights from Pristina (PRN) to Easton (ESN)
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Flights from St. Louis (STL) to Easton (ESN)
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Flights from Toronto (YYZ) to Annapolis (ANP)
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Allen Pond Park
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Chesapeake Bay Bridge
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Visit Crofton
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Dorchester County Visitors Center
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Fruitland Holidays
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Visit South Gate
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Historical Society of Kent County Maryland
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Kunta Kinte–Alex Haley Memorial
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Visit Largo
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London Town
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Long Wharf Park
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Maryland Holidays
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Visit North Beach
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Pasadena Holidays
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Prince George's Stadium
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Queenstown Harbor Golf Club
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Rolphs Wharf Marina
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Rose Haven Holidays
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Spocott Windmill
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Visit Tilghman
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U.s. Naval Academy
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Wilmer Park
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Visit Wingate
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Wor-Wic Community College
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Car hire near Anchorage
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Car hire Arnold
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Car hire near Bill Burton Fishing Pier State Park
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Car hire California
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Car hire near Kunta Kinte–Alex Haley Memorial
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Car hire Queenstown
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Things to do in Annapolis
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Things to do in Chesapeake Beach
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Search Private Holiday Homes in Eastern Shore

Change your mind

Treat yourself

Be picky

Find holiday rentals that suit your style

Check prices for these dates

Learn more about Eastern Shore

Explore a world of travel with Expedia