Book Holiday Homes in Annapolis
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Featured Holiday Homes in Annapolis
Directly Across from Gate One & Steps from the Waterfront
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Recently Renovated Annapolis Home - Conveniently Located
3 Story Stunner in Murray Hill <1 mile from USNA!
Your Annapolis Adventure Starts Here!!
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Charming Historic Townhouse Steps From USNA
La Maison - Stunning waterfront views with pool
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 | 271 Holiday Homes |
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Lowest Price | AU$178 |
Highest Price | AU$253 |
Popular accommodation | Directly Across from Gate One & Steps from the Waterfront , Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, Recently Renovated Annapolis Home - Conveniently Located, 3 Story Stunner in Murray Hill <1 mile from USNA!, Your Annapolis Adventure Starts Here!! , Charming garden row home, easy 4 block walk to the heart of Annapolis., Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, Charming Historic Townhouse Steps From USNA, La Maison - Stunning waterfront views with pool |
Top Locations for Holiday Homes in Annapolis
Top trending hotels in Annapolis
Historic Inns of Annapolis
Graduate by Hilton Annapolis
Hilton Garden Inn Annapolis Downtown
DoubleTree by Hilton Hotel Annapolis
More ways to explore Annapolis
Top picks
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.