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!

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!
Historic Annapolis Home 1.5 blocks from center of town.

Historic Annapolis Home 1.5 blocks from center of town.

Annapolis
A stay at this vacation home places you in the heart of Annapolis, within a 15-minute walk of U.S. Naval Academy and Spa Creek.
Historic Annapolis Home 1.5 blocks from center of town.
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!!
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Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

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

2 out of 5
Annapolis
With a stay at this vacation home in Annapolis (Oyster Harbor), you'll be within a 15-minute drive of U.S. Naval Academy and Bay Bridge Market Place Shopping ...
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Steps to USNA Gate 3 at historic Gatehouse, on-site parking

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

2.5 out of 5
Annapolis
Steps to USNA Gate 3 at historic Gatehouse, on-site parking is in the heart of Annapolis, within a 5-minute walk of St. John's College and U.S. Naval ...
Steps to USNA Gate 3 at historic Gatehouse, on-site parking
PERFECT LOCATION in the heart of history

PERFECT LOCATION in the heart of history

Annapolis
With a stay at this vacation home, you'll be centrally located in Annapolis, steps from U.S. Naval Academy and John Smith House.
PERFECT LOCATION in the heart of history
7 mins away from Downtown Annapolis

7 mins away from Downtown Annapolis

Annapolis
With a stay at this vacation home in Annapolis, you'll be within a 10-minute drive of U.S. Naval Academy and Historic Mount Moriah AME Church.
7 mins away from Downtown Annapolis
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

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

Annapolis
With a stay at this vacation home, you'll be centrally located in Annapolis, within a 5-minute walk of U.S. Naval Academy and William Paca House.
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.

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 Hammond-Harwood House.
Charming garden row home, easy 4 block walk to the heart of 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.

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
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 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$318 per night from 13 Apr to 14 Apr
AU$318
includes taxes & fees
13 Apr - 14 Apr
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
The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$270 per night from 6 Apr to 7 Apr
AU$270
includes taxes & fees
6 Apr - 7 Apr
With a stay at The Westin Annapolis in Annapolis, you'll be in the historical district, within a 5-minute drive of U.S. Naval Academy and People's Brewer Hill ...
The Westin Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd, Annapolis, MD
Fully refundable
The price is AU$183 per night from 6 Apr to 7 Apr
AU$183
includes taxes & fees
6 Apr - 7 Apr
Located in Annapolis, Crowne Plaza Annapolis by IHG is a 4-minute walk from Westfield Annapolis Mall and 14 minutes by foot from Anne Arundel Medical ...
Crowne Plaza Annapolis by IHG
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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$153 per night from 20 Apr to 21 Apr
AU$153
includes taxes & fees
20 Apr - 21 Apr
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
Don't see what you're looking for?
See all available properties in 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.