Chesapeake Bay Vacation Rentals

Vacation rental homes designed to bring you & your loved ones together for an unforgettable experience.

Make Chesapeake Bay your next getaway

The Chesapeake is the largest estuary in the United States, and life along its shoreline still runs on tides, crab pots, and sailboats. The Eastern Shore keeps small harbor towns like St. Michaels and Oxford, where skipjacks are tied up beside oyster houses, while Annapolis anchors the western side with its colonial streets and naval academy. Bring an appetite for blue crab and a tolerance for slow afternoons on the water.

Exactly what you're looking for

Chesapeake Bay vacation rentals for large groups

Chesapeake Bay pet-friendly vacation rentals

Chesapeake Bay vacation rentals with a hot tub

Discover your dream vacation home in Chesapeake Bay

Bay Estate・Dameron
7 Bedrooms
5 Bathrooms
16 Guests
More properties are coming

We are constantly working on increasing our portfolio & more homes will be available soon. You can explore other regions for now.

Frequently asked questions about Chesapeake Bay

  • Sailing
  • Crabbing
  • Fishing
  • Kayaking
  • Waterfront dining
  • Historic harbor towns
  • Birdwatching

Summers are warm and humid with highs in the upper 80s, ideal for boating and swimming. Spring and fall are mild and pleasant, and winters are cold in the 30s and 40s, when the harbor towns go quiet.

Baltimore/Washington International (BWI) is the main gateway, with Reagan National (DCA) and Dulles (IAD) also within reach. A car is essential, since the shoreline is long and crossing between the western and eastern shores means the Bay Bridge. Once you are in a harbor town, everything is usually walkable.

  • Historic Annapolis and the City Dock
  • St. Michaels and the Chesapeake Bay Maritime Museum
  • Sailing charters and sunset cruises
  • Blackwater National Wildlife Refuge
  • Oxford and the Oxford-Bellevue Ferry
  • Kayaking the tidal creeks
  • Crab houses along the Eastern Shore

Own a vacation rental property?

Thinking about spending more time in Chesapeake Bay? If you’re also exploring vacation rental management in Chesapeake Bay or looking for support managing a property, here’s how AvantStay helps owners.

Explore Management Services

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