Book Holiday Homes in Chesapeake Bay

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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
Holiday Homes
Lowest Price
NZ$203
Highest Price
NZ$312
Popular accommodation
Renaissance Baltimore Harborplace Hotel, Washington Plaza Hotel, Hamilton Hotel Washington DC, Omni Shoreham Hotel

Top trending hotels in Chesapeake Bay

Renaissance Baltimore Harborplace Hotel

Renaissance Baltimore Harborplace Hotel

4 out of 5
202 E Pratt St, Baltimore, MD
Fully refundableReserve now, pay when you stay
The price is NZ$228 per night from 21 Jan to 22 Jan
NZ$228
includes taxes & fees
21 Jan - 22 Jan 2025
Book a stay at this business-friendly hotel in Baltimore. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the helpful staff ...
Renaissance Baltimore Harborplace Hotel
Washington Plaza Hotel

Washington Plaza Hotel

4 out of 5
10 Thomas Circle NW, Washington, DC
Fully refundableReserve now, pay when you stay
The price is NZ$203 per night from 24 Dec to 25 Dec
NZ$203
includes taxes & fees
24 Dec - 25 Dec
Book a stay at this business-friendly hotel in Washington. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the breakfast and the ...
Washington Plaza Hotel
Hamilton Hotel Washington DC

Hamilton Hotel Washington DC

4 out of 5
1001 14th St NW, Washington, DC
Fully refundableReserve now, pay when you stay
The price is NZ$290 per night from 24 Dec to 25 Dec
NZ$290
includes taxes & fees
24 Dec - 25 Dec
Book a stay at this business-friendly hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the restaurant and ...
Hamilton Hotel Washington DC
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Omni Shoreham Hotel

Omni Shoreham Hotel

4 out of 5
2500 Calvert St Nw, Washington, DC
Fully refundableReserve now, pay when you stay
The price is NZ$312 per night from 24 Dec to 25 Dec
NZ$312
includes taxes & fees
24 Dec - 25 Dec
Stay at this 4-star family-friendly hotel in Washington. Enjoy an outdoor pool, 2 bars/lounges, and breakfast (surcharge). Our guests praise the pool and the ...
Omni Shoreham Hotel
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.