Book Holiday Homes in Annapolis

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Featured Holiday Homes in Annapolis

Directly Across from Gate One & Steps from the Waterfront

Directly Across from Gate One & Steps from the Waterfront

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 Gate One & Steps from the Waterfront
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Annapolis
With a stay at this vacation home in Annapolis (Cape Saint Claire), you'll be within a 15-minute drive of U.S. Naval Academy and Sandy Point State Park.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Recently Renovated Annapolis Home - Conveniently Located

Recently Renovated Annapolis Home - Conveniently Located

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 ...
Recently Renovated Annapolis Home - Conveniently Located
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3 Story Stunner in Murray Hill <1 mile from USNA!

3 Story Stunner in Murray Hill <1 mile from USNA!

Annapolis
With a stay at this vacation home in Annapolis (Murray Hill), you'll be within a 5-minute drive of U.S. Naval Academy and Annapolis Civil Rights Plaque.
3 Story Stunner in Murray Hill <1 mile from USNA!
Your Annapolis Adventure Starts Here!!

Your Annapolis Adventure Starts Here!!

Annapolis
With a stay at this vacation home, you'll be centrally located in Annapolis, within a 10-minute drive of U.S. Naval Academy and Bay Bridge Market Place Shopping ...
Your Annapolis Adventure Starts Here!!
Charming garden row home, easy 4 block walk to the heart of Annapolis.

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Annapolis
With a stay at this vacation home in Annapolis (Historic District), you'll be within a 5-minute walk of U.S. Naval Academy and Chase Lloyd House.
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

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Annapolis
With a stay at this vacation home in Annapolis (Admiral Heights), you'll be within a 5-minute drive of U.S. Naval Academy and Navy-Marine Corps Memorial ...
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
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
La Maison - Stunning waterfront views with pool

La Maison - Stunning waterfront views with pool

Annapolis
With a stay at this vacation home in Annapolis (Cape St. John), you'll be within a 15-minute drive of U.S. Naval Academy and Broad Creek Marsh.
La Maison - Stunning waterfront views with pool
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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.

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
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 trending hotels in Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$233 per night from 24 Nov to 25 Nov
AU$233
includes taxes & fees
24 Nov - 25 Nov
With a stay at Historic Inns of Annapolis, you'll be centrally located in Annapolis, steps from The Colonial Players and Thurgood Marshall Memorial.
Historic Inns of Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$253 per night from 18 Dec to 19 Dec
AU$253
includes taxes & fees
18 Dec - 19 Dec
With a stay at Graduate by Hilton Annapolis, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and Annapolis Civil Rights ...
Graduate by Hilton Annapolis
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$192 per night from 16 Dec to 17 Dec
AU$192
includes taxes & fees
16 Dec - 17 Dec
With a stay at Hilton Garden Inn Annapolis Downtown, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and Annapolis Civil ...
Hilton Garden Inn Annapolis Downtown
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DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$178 per night from 25 Nov to 26 Nov
AU$178
includes taxes & fees
25 Nov - 26 Nov
With a stay at DoubleTree by Hilton Hotel Annapolis in Annapolis, you'll be in the business district, within a 5-minute drive of U.S. Naval Academy and The Kunta ...
DoubleTree by Hilton Hotel Annapolis
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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.