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

Tip Of The Town Fresh and New 3 Bedroom Nest

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

Sailor's Sunrise Cottage - Chesapeake Bay

Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Chesapeake Point | Waterfront w/ HOT TUB + Beach!
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 | 158 Holiday Homes |
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Lowest Price | NZ$126 |
Highest Price | NZ$465 |
Popular accommodation | Tip Of The Town Fresh and New 3 Bedroom Nest, Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!, Sailor's Sunrise Cottage - Chesapeake Bay, Charming 2-bedroom house with WiFi, AC in marvelous Wilmington, Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!, Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6, Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio, Lark's Nest on the Chester River. Spacious, waterfront home with private dock., Chesapeake Point | Waterfront w/ HOT TUB + Beach! |
Top trending hotels in Chesapeake City

Historic Chesapeake City Stay

Embassy Suites by Hilton Newark Wilmington South

Red Roof Inn & Suites Newark - University

Sonesta Select Newark Christiana Mall
More ways to explore Chesapeake City
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^Subject to availability and chosen travel dates.