Vacation Homes in Chesapeake Beach
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Featured Vacation Homes in Chesapeake Beach

Sweet Bamboo Beach Cottage

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

The Blue Crab Beach House - Free beach passes

Private Waterview Estate with 4 bedroom Suites, game room and Hot Tub

The Lazy Crab Beach House - Free beach passes

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

Time Stands Still At the Dock.

7 mins away from Downtown Annapolis

Your Annapolis Adventure Starts Here!!

25-50% Off~Private Beach~Hot Tub~Fire Table~

Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Top trending hotels in Chesapeake Beach

Mid-Century Modern on Private Beach, Designed by Award Winning Architect!
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 | 320 Vacation Homes |
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Lowest Price | CA $131 |
Highest Price | CA $557 |
Popular accommodation | Sweet Bamboo Beach Cottage, Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub, The Blue Crab Beach House - Free beach passes , Private Waterview Estate with 4 bedroom Suites, game room and Hot Tub, The Lazy Crab Beach House - Free beach passes , Rockhold Creek Cottage, Water Front, Vacation Home, Docks, Time Stands Still At the Dock., 7 mins away from Downtown Annapolis, Your Annapolis Adventure Starts Here!! , 25-50% Off~Private Beach~Hot Tub~Fire Table~, Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks, Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock! |