Top Vacation Rentals in Chesapeake Bay ᐅ Instant booking

Mariners Cove Waterfront - Private Dock, Pet Friendly, Wi-Fi, Off-Street Parking

0.7 mi to the beach

Sleeps 12 pers.3 bedrooms3,498 ft²

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Circa 1900 Home in the Heart of Historic Downtown Chestertown

Sleeps 6 pers.4 bedrooms

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Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Sleeps 6 pers.3 bedrooms1,270 ft²

Waterfront Wildlife Retreat on the Patuxent River

5.1 mi to the beach

Sleeps 6 pers.3 bedrooms1,593 ft²

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Captivating Chesapeake experience

2 mi to the beach

Sleeps 6 pers.2 bedrooms1,453 ft²

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Historic Chapel Views, Steps to Usna Gate 1 w Private Patio & Off-Site Parking

0.9 mi to the beach

Sleeps 7 pers.3 bedrooms2,411 ft²

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Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!

2.5 mi to the beach

Sleeps 5 pers.3 bedrooms2,293 ft²

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Waterfront Getaway with Dock

Sleeps 6 pers.3 bedrooms

American Four-Square completely renovated, easy walk to the beach!

5.3 mi to the beach

Sleeps 6 pers.3 bedrooms1,798 ft²

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Sweet Bamboo Beach Cottage

Sleeps 6 pers.3 bedrooms958 ft²

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Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!

2.9 mi to the beach

Sleeps 4 pers.2 bedrooms1,292 ft²

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The Blue Crab Beach House - Free beach passes 🦀

Sleeps 4 pers.2 bedrooms797 ft²

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Annapolis Condominium in the heart of the historic center

1.2 mi to the beach

Sleeps 6 pers.3 bedrooms1,399 ft²

Cozy Cottage - quaint and comfy - 5 blocks to the beach, 1 block to Mason Ave.

5.5 mi to the beach

Sleeps 7 pers.3 bedrooms

YardTerraceParkingInternet

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

2.2 mi to the beach

Sleeps 7 pers.4 bedrooms

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Apartment Ice Ice Baby in Newport News

Apartment The Safe House in Newport News

Park Place - Comfy Condo Close to Beach

Apartment The SpeakEasy in Newport News

Buckroe Bungalow in Hampton

Apartment Breakfast @ Tiffany's in Newport News

Adorable Chesapeake Bay Beach Cottage B Just 1 Block from the Sand!

The 1850 House with Deck in Quantico

Flat 207 with Fireplace in Saint Michaels

Apartment in Newport News

Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Studio in Hampton

The BeeHive with Fireplace in Newport News

Sunny Shores Retreat with Private Pool

Mariners Cove Waterfront - Private Dock, Pet Friendly, Wi-Fi, Off-Street Parking

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Waterfront Wildlife Retreat on the Patuxent River

Captivating Chesapeake experience

Historic Chapel Views, Steps to Usna Gate 1 w Private Patio & Off-Site Parking

Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!

Waterfront Getaway with Dock

American Four-Square completely renovated, easy walk to the beach!

Sweet Bamboo Beach Cottage

Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!

The Blue Crab Beach House - Free beach passes 🦀

Annapolis Condominium in the heart of the historic center

Cozy Cottage - quaint and comfy - 5 blocks to the beach, 1 block to Mason Ave.

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown