Book Holiday Homes in Annapolis
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Featured Holiday Homes in Annapolis

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

Historic Annapolis Home 1.5 blocks from center of town.

Your Annapolis Adventure Starts Here!!

Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

Steps to USNA Gate 3 at historic Gatehouse, on-site parking

PERFECT LOCATION in the heart of history

7 mins away from Downtown Annapolis

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Charming garden row home, easy 4 block walk to the heart of Annapolis.
Annapolis 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 Annapolis vacation homes are the perfect way for you to wing it.
Holiday houses in Annapolis 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 Annapolis 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 Annapolis adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Annapolis 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 Annapolis 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.
Annapolis Holiday Homes essential information
Accommodation | 342 Holiday Homes |
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Lowest Price | AU$153 |
Highest Price | AU$318 |
Popular accommodation | Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Historic Annapolis Home 1.5 blocks from center of town., Your Annapolis Adventure Starts Here!! , Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks, Steps to USNA Gate 3 at historic Gatehouse, on-site parking, PERFECT LOCATION in the heart of history, 7 mins away from Downtown Annapolis, Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything, Charming garden row home, easy 4 block walk to the heart of Annapolis. |
Top Locations for Holiday Homes in Annapolis
Top trending hotels in Annapolis

Historic Inns of Annapolis

The Westin Annapolis

Crowne Plaza Annapolis by IHG

Hilton Garden Inn Annapolis Downtown
More ways to explore Annapolis
Top picks
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^Subject to availability and chosen travel dates.