Book Holiday Homes in Chesapeake Bay
More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)
We keep it easy with the option to pay now or later on select accommodation
Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Chesapeake Bay
Spacious 4-bedroom townhome in brilliant Washington with WiFi, AC
Serenity on the Bay-Complimentary Sunrise & Sunset Views
The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer
Blufin Bungalows & Marina
Parking & Onsite Retail | Steps from Metro RL | Washington DC
Visit Historic Sites | Metro & Union Station Nearby | NoMa
4BR/4BA Beautiful and Large House in DC! 1 Mile from Capitol Hill!
⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
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 | 447 Holiday Homes |
---|---|
Lowest Price | AU$184 |
Highest Price | AU$824 |
Popular accommodation | Spacious 4-bedroom townhome in brilliant Washington with WiFi, AC, Serenity on the Bay-Complimentary Sunrise & Sunset Views, The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer, Blufin Bungalows & Marina, Parking & Onsite Retail | Steps from Metro RL | Washington DC, Visit Historic Sites | Metro & Union Station Nearby | NoMa, 4BR/4BA Beautiful and Large House in DC! 1 Mile from Capitol Hill!, ⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino, Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! |
Holiday Homes in Chesapeake Bay
Top Locations for Holiday Homes in Chesapeake Bay
More accommodations in Chesapeake Bay
Top trending hotels in Chesapeake Bay
Renaissance Baltimore Harborplace Hotel
Washington Plaza Hotel
Hamilton Hotel Washington DC
Omni Shoreham Hotel
More ways to explore Chesapeake Bay
Top picks
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.