Book Holiday Homes in Chesapeake City
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Featured Holiday Homes in Chesapeake City

Sailor's Sunrise Cottage - Chesapeake Bay

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Where luxury meets laughter by the bay. Welcome to Bamboo Sands Villa & Captain’s Quarters.

Luxurious and spacious townhome with all necessary amenities awaits your stay.

Sunset River Shack -amazing waterfront view

Chesapeake Bay House with Dock & Private Beach

5-bedroom vacation home 5 minutes from historic Charlestown

Beachfront Sunsets on the Water at Oakwood Beach

Cozy home w/fenced in yard-Dog Friendly with Pet fee. 2 block walk to downtown!
Chesapeake City Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chesapeake City vacation homes are the perfect way for you to wing it.
Holiday houses in Chesapeake City let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chesapeake City in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chesapeake City adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chesapeake City with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chesapeake City vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Chesapeake City Holiday Homes essential information
Accommodation | 149 Holiday Homes |
|---|---|
Lowest Price | NZ$128 |
Highest Price | NZ$944 |
Popular accommodation | Sailor's Sunrise Cottage - Chesapeake Bay, Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach, Where luxury meets laughter by the bay. Welcome to Bamboo Sands Villa & Captain’s Quarters., Luxurious and spacious townhome with all necessary amenities awaits your stay., Sunset River Shack -amazing waterfront view, Chesapeake Bay House with Dock & Private Beach, 5-bedroom vacation home 5 minutes from historic Charlestown, Beachfront Sunsets on the Water at Oakwood Beach, Cozy home w/fenced in yard-Dog Friendly with Pet fee. 2 block walk to downtown! |
Top trending hotels in Chesapeake City

Quality Inn Newark - Wilmington

Sonesta Select Newark Christiana Mall

Red Roof Inn & Suites Newark - University

Great Wolf Lodge Perryville
More ways to explore Chesapeake City
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^Subject to availability and chosen travel dates.
