Chesapeake Beach Vacation Rentals

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Vacation Rentals in Chesapeake Beach

Private Pool & Stunning Bay Views on Kent Island

Stevensville MD

With a stay at this vacation home in Stevensville, you'll be steps from Chesapeake Bay and Northern Chesapeake Bay.

Pool

Kitchen

Charming Annapolis WaterVIEW Home

Annapolis MD

$714 nightly

$814 total

Jun 29 - Jun 30

Total with taxes and fees

With a stay at this vacation home in Annapolis (Arundel on the Bay), you'll be within a 15-minute drive of Chesapeake Bay and Annapolis City Dock.

Grace Cottage, St Michaels Walk to everything!

Saint Michaels MD

A stay at this vacation home places you in the heart of St. Michaels, steps from Muskrat Park and Saint Marys Square.

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Shady Side MD

With a stay at this vacation home in Shady Side, you'll be within a 10-minute drive of Chesapeake Bay and Shadyside Park.

Kitchen

Washer

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Cambridge MD

With a stay at this vacation home in Cambridge, you'll be on the waterfront, within a 15-minute drive of Chesapeake Bay and Spocott Windmill.

Eastport Cottage .5 mi from Downtown Annapolis

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, within a 5-minute drive of Annapolis City Dock and U.S. Naval Academy.

8,000 Sq Ft Luxury Estate Near Annapolis | Sleeps 32 | Pool, Theater & Pickleball

Davidsonville MD

With a stay at this vacation home in Davidsonville, you'll be within a 15-minute drive of U.S. Naval Academy and Patuxent River.

Pool

Kitchen

Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

Mechanicsville MD

With a stay at this vacation home in Mechanicsville, you'll be within a 15-minute drive of John Baggett Park at Laurel Grove and Laurel Ridge Park.

Waterfront Escape with Pool Nature Lover Paradise

Stevensville MD

With a stay at this vacation home in Stevensville, you'll be within a 5-minute drive of Chesapeake Bay and Northern Chesapeake Bay.

Discover tranquility near Calvert Cliffs

Saint Leonard MD

Located in St. Leonard, this vacation home is on the waterfront, within a 10-minute drive of Perigeaux Vineyards and Winery and Jefferson Patterson Park and Museum.

Bayfront Escape in Edgewater with Deck, Balcony, and Walk to Beach

Edgewater MD

When you stay at this vacation home in Edgewater, you'll be on the waterfront, just steps from Chesapeake Bay and Northern Chesapeake Bay.

Waterfront Home with Private Dock, Community Beach

Annapolis MD

With a stay at this vacation home in Annapolis (Oyster Harbor), you'll be within a 15-minute drive of Chesapeake Bay and U.S. Naval Academy.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.