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Featured Holiday Homes in North Beach

Charming Historic Townhouse Steps From USNA

Charming Historic Townhouse Steps From USNA

Annapolis
This vacation home is in the heart of Annapolis, within a 5-minute walk of St. John's College and U.S. Naval Academy.
Charming Historic Townhouse Steps From USNA
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

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

Annapolis
A stay at this vacation home places you in the heart of Annapolis, steps from U.S. Naval Academy and Annapolis City Dock.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!

North Beach
Located in Owings, this vacation home is a 3-minute drive from Bayside History Museum and 6 minutes from Chesapeake Beach Water Park.
The Cozy Crab- Your Charming Haven in Lovely North Beach!
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421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Annapolis
With a stay at this vacation home, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and Annapolis Harbor.
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

2.5 out of 5
Annapolis
With a stay at this vacation home, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and People's Brewer Hill ...
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill

The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill

Stevensville
When you stay at this vacation home in Stevensville, you'll be within a 10-minute drive of Matapeake State Park and Romancoke Wharf County Park.
The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

St. Michaels
When you stay at this vacation home in St. Michaels, you'll be on the waterfront, within a 5-minute drive of Perry Cabin Park and Saint Michaels Town Hall.
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Cozy Annapolis Cottage

Cozy Annapolis Cottage

Annapolis
With a stay at this vacation home, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and Navy-Marine Corps Memorial ...
Cozy Annapolis Cottage
Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.

Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.

Annapolis
With a stay at this vacation home, you'll be centrally located in Annapolis, within a 15-minute drive of U.S. Naval Academy and Bay Bridge Market Place Shopping ...
Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.
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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.

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

Holiday houses in North 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 North 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 North Beach adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in North 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 North 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.

North Beach Holiday Homes essential information

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553 Holiday Homes
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Popular accommodation
Charming Historic Townhouse Steps From USNA, Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , The Cozy Crab- Your Charming Haven in Lovely North Beach!, 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!, Charming Downtown Annapolis. Stroll to all the Historic District has to offer. , The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill, Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly, Cozy Annapolis Cottage, Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.

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^Subject to availability and chosen travel dates.