Book Holiday Homes in Chesapeake Beach

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Chesapeake Beach 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 Beach vacation homes are the perfect way for you to wing it.

Holiday houses in Chesapeake Beach 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 Beach 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 Beach adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chesapeake Beach 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 Beach 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 Beach Holiday Homes essential information

Accommodation
Holiday Homes
Lowest Price
AU$115
Highest Price
AU$768
Popular accommodation
Rod 'N' Reel Resort, Mid-Century Modern on Private Beach, Designed by Award Winning Architect!, Family Beach House: Spacious Deck, Grill & Views, Econo Lodge Andrews Air Force Base

Top trending hotels in Chesapeake Beach

Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave, Chesapeake Beach, MD
Fully refundableReserve now, pay when you stay
The price is AU$229 per night from 2 Mar to 3 Mar
AU$229
includes taxes & fees
2 Mar - 3 Mar
When you stay at Rod 'N' Reel Resort in Chesapeake Beach, you'll be on the waterfront, just steps from Chesapeake Beach Railway Museum and 3 minutes by foot ...
Rod 'N' Reel Resort
Mid-Century Modern on Private Beach, Designed by Award Winning Architect!

Mid-Century Modern on Private Beach, Designed by Award Winning Architect!

Chesapeake Beach
Located in Chesapeake Beach, this vacation home is on the waterfront, a 4-minute drive from Bruce Gabrielson's Surf Art Gallery and Museum and 5 minutes from ...
Mid-Century Modern on Private Beach, Designed by Award Winning Architect!
Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views

Chesapeake Beach
The price is AU$768 per night from 10 Mar to 11 Mar
AU$768
includes taxes & fees
10 Mar - 11 Mar
With a stay at this vacation home in Chesapeake Beach, you'll be on the beach, just steps from Breezy Point Beach and a 4-minute drive from Bruce Gabrielson's ...
Family Beach House: Spacious Deck, Grill & Views
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Econo Lodge Andrews Air Force Base

Econo Lodge Andrews Air Force Base

2 out of 5
7851 Malcolm Road, Clinton, MD
Fully refundableReserve now, pay when you stay
The price is AU$115 per night from 16 Feb to 17 Feb
AU$115
includes taxes & fees
16 Feb - 17 Feb
With a stay at Econo Lodge Andrews Air Force Base, you'll be centrally located in Clinton, within a 15-minute drive of MGM National Harbor Casino and The Theater ...
Econo Lodge Andrews Air Force Base
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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.