Book Holiday Homes in Chesapeake Bay
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Featured Holiday Homes in Chesapeake Bay

Blufin Bungalows & Marina

Spacious 4-bedroom townhome in brilliant Washington with WiFi, AC

Your own private beach with this charming 3-bedroom beachfront house!

Bright, spacious house with private, scenic backyard in Arlington Forest

"Pura Vida" Fabulous 4 Bed Home near H St & Union Market

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Super close to beaches, the historic triangle, and bush gardens!

Charming 2-bedroom house in fantastic Takoma Park with WiFi, AC

Downtown, Sleeps 9, Dog-friendly, Short Walk to the Beach
Chesapeake Bay 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 Bay vacation homes are the perfect way for you to wing it.
Holiday houses in Chesapeake Bay 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 Bay 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 Bay adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chesapeake Bay 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 Bay 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 Bay Holiday Homes essential information
Accommodation | 640 Holiday Homes |
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Lowest Price | AU$216 |
Highest Price | AU$961 |
Popular accommodation | Blufin Bungalows & Marina, Spacious 4-bedroom townhome in brilliant Washington with WiFi, AC, Your own private beach with this charming 3-bedroom beachfront house!, Bright, spacious house with private, scenic backyard in Arlington Forest, "Pura Vida" Fabulous 4 Bed Home near H St & Union Market, Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Super close to beaches, the historic triangle, and bush gardens!, Charming 2-bedroom house in fantastic Takoma Park with WiFi, AC, Downtown, Sleeps 9, Dog-friendly, Short Walk to the Beach |
Top Locations for Holiday Homes in Chesapeake Bay
More accommodations in Chesapeake Bay
Top trending hotels in Chesapeake Bay

Washington Plaza Hotel

State Plaza Hotel

Hilton Garden Inn Reagan National Airport

Holiday Inn Washington Capitol - Natl Mall by IHG
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^Subject to availability and chosen travel dates.