Book Holiday Homes in Annapolis
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Featured Holiday Homes in Annapolis
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
NEW, cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown
Pet Friendly - Stone's throw from Annapolis City Dock with private back patio
Cozy suite Located in Presidents Hill
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
Historic Annapolis Home!
Directly Across from Gate One & Steps from the Waterfront
Recently Renovated Annapolis Home - Conveniently Located
Charming Cottage with Hot Tub 1 Block from the Bay
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 | 284 Holiday Homes |
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Lowest Price | AU$202 |
Highest Price | AU$950 |
Popular accommodation | Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, NEW, cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown, Pet Friendly - Stone's throw from Annapolis City Dock with private back patio, Cozy suite Located in Presidents Hill, Cozy Cottage by the Beach - Waterview Minutes from Downtown Annapolis , Historic Annapolis Home!, Directly Across from Gate One & Steps from the Waterfront , Recently Renovated Annapolis Home - Conveniently Located, Charming Cottage with Hot Tub 1 Block from the Bay |
Top Locations for Holiday Homes in Annapolis
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Graduate Annapolis
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^Subject to availability and chosen travel dates.