Vacation Homes in Chesapeake Beach
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Featured Vacation Homes in Chesapeake Beach

The Blue Crab Beach House - Free beach passes

Modern Waterfront House with Amazing views!

Sweet Bamboo Beach Cottage

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

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

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

The Lazy Crab Beach House - Free beach passes

Relax on Kent Island in 3 Bedroom Home w/Waterview

The Cottage

7 mins away from Downtown Annapolis
Top trending hotels in Chesapeake Beach

Family Beach House: Spacious Deck, Grill & Views
Vacation Rentals in Chesapeake Beach
What kind of vacation do you want in Chesapeake Beach? The answer to that question will help you choose the right lodging for your stay. The wise wanderer knows that a vacation rental is an essential part of the traveling experience. It’s more than just a place to crash at night—it’s where you wake up in the morning, where you lounge when you’re not exploring, and it’s the starting point for all your adventures. No matter what type of vacation homes strike your fancy, Travelocity has something in Chesapeake Beach that will speak to you.
Do you want a fully equipped kitchen so you can exercise your culinary mastery and impress your travel buddies? How about a romantic terrace for your anniversary trip? Have you always wished to fall asleep to the sound of waves crashing on the shore? One of our vacation home rentals is bound to add that extra magic to your trip. In fact, we’ve got plenty of options lined up just for you in Chesapeake Beach, including luxury vacation rentals. On a budget? We can work with your funds and still give you a great place to sleep at night.
Take a look at what we have on offer. You’ll find rentals close to the big tourist draws, as well as rentals that keep you away from the crowd. Consider vacation rentals a little off the beaten path where you can live like a local and discover hidden gems that never make it to the tourist sites. Book through Travelocity and start your getaway today.
Chesapeake Beach Vacation Homes essential information
Accommodation | 410 Vacation Homes |
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Lowest Price | CA $133 |
Highest Price | CA $636 |
Popular accommodation | The Blue Crab Beach House - Free beach passes , Modern Waterfront House with Amazing views!, Sweet Bamboo Beach Cottage, Rockhold Creek Cottage, Water Front, Vacation Home, Docks, Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier, Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks, The Lazy Crab Beach House - Free beach passes , Relax on Kent Island in 3 Bedroom Home w/Waterview, The Cottage , 7 mins away from Downtown Annapolis, Walk to Everything House |