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Popular Annapolis Vacation Rentals

Find the perfect Annapolis vacation rental

House Annapolis
from $388 per night
12 guests ∙ 5 bedrooms

House

5.0
Outstanding(53 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
from $874 per night
House ∙ 10 guests ∙ 5 bedrooms

311 m² House

5.0
Outstanding(66 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
from $229 per night
12 guests ∙ 5 bedrooms

House

4.7
Excellent(3 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
from $857 per night
12 guests ∙ 5 bedrooms

House

5.0
Outstanding(9 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Apartment Annapolis
from $121 per night
4 guests ∙ 2 bedrooms

Apartment

5.0
Outstanding(11 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
from $624 per night
10 guests ∙ 4 bedrooms

House

5.0
Outstanding(3 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
from $514 per night
6 guests ∙ 3 bedrooms

House

5.0
Outstanding(8 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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House Annapolis
from $1,366 per night
House ∙ 15 guests ∙ 6 bedrooms

743 m² House

5.0
Outstanding(31 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Cottage Annapolis
from $245 per night
4 guests ∙ 2 bedrooms

Cottage

5.0
Outstanding(2 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Vacation rentals with Wi-Fi

House  Annapolis
from $693 per night
House ∙ 10 guests ∙ 5 bedrooms

325 m² House

5.0
Outstanding(98 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Internet
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House  Annapolis
from $1,724 per night
House ∙ 12 guests ∙ 6 bedrooms

604 m² House

4.9
Outstanding(18 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Internet
Vrbo
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House  Annapolis
from $731 per night
10 guests ∙ 5 bedrooms

House

5.0
Outstanding(28 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Internet
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Vacation rentals and apartments with air conditioning

House  Annapolis
from $373 per night
House ∙ 20 guests ∙ 4 bedrooms

372 m² House

5.0
Outstanding(12 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
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House  Annapolis
from $515 per night
19 guests ∙ 5 bedrooms

House

4.9
Outstanding(33 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
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House  Annapolis
from $355 per night
House ∙ 10 guests ∙ 5 bedrooms

139 m² House

5.0
Outstanding(54 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
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Apartments and vacation rentals with a kitchen

House  Annapolis
from $446 per night
House ∙ 6 guests ∙ 3 bedrooms

78 m² House

5.0
Outstanding(10 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Kitchen
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House  Annapolis
from $595 per night
11 guests ∙ 5 bedrooms

House

5.0
Outstanding(59 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Kitchen
Vrbo
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House  Annapolis
from $224 per night
House ∙ 8 guests ∙ 4 bedrooms

183 m² House

4.8
Outstanding(128 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Kitchen
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Frequently Asked Questions

What is the average price per night for accommodation in Annapolis?

Accommodation in Annapolis cost from $120 per night.

Are there any vacation rentals available to book in Annapolis?

Our large collection of vacation homes makes it easy to filter and compare 1,392 offers in Annapolis.

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Annapolis Information

About Annapolis

Maryland’s capital, Annapolis, is home to the United States Naval Academy, the oldest state house in the nation and many historical meetings before and after the American Revolution. This picturesque city sits on the mouth of the Severn River, overlooking the Chesapeake Bay. It’s also home to the small St. John’s college, making this corner of the Baltimore-Washington metro area a prime all-ages destination for dining, culture and sightseeing.

Things To Do In Annapolis

There are many great things to do here in such a small area: history buffs will appreciate a tour of the Maryland State House, where the Continental Congress met in 1783 to end the Revolutionary War. There’s also the William Paca House and Garden, a Georgian mansion in the center of town that has two acres of flora and fauna perfect for an impromptu photo shoot. Visit the Banneker-Douglass Museum (inside of an old Episcopal church) to absorb crucial Maryland African-American history, or the Naval Academy Museum, which is full of ship replicas and displays of Revolutionary War battlefields.

Day Trips From Annapolis

There’s always the adjacent big cities of Baltimore and DC, but if you’re looking for a low-key jaunt, think of getting out into nature at Blackwater National Refuge south on Highway 50. There, you may find birds like owls, herons and even bald eagles, and it’s right next to the significant Harriet Tubman Underground Railroad National Park (and monument). About an hour north in Chestertown, Cassinelli Winery & Vineyards has a wide selection of not only wine and cider, but house-made apple brandy, corn whiskey, gin and vodka.

Accommodations In Annapolis

Annapolis isn’t known for having distinct neighborhoods, but you’re likely to find rentals in the heart of town next to the Naval Academy and the Annapolis Harbour. There are plenty of historic homes and townhouses near diverse dining options. For roughly the same price per night, you can take a truly unique-to-the-Chesapeake plan of action and stay in a luxury yacht, allowing you and your guests to enjoy the gorgeous sunrises and sunsets during the stay.

Transportation in Annapolis

The nearest airports are both within an hour from Annapolis—Baltimore/Washington International Airport (BWI) is a 30-minute drive into town, while Ronald Reagan National Airport (DCA) is 45 minutes away. Once in the city, Uber and Lyft can take you not just across town, but to nearby areas in the metro area.

What are the trendiest neighborhoods in Annapolis?

Popular Day Trips Near Annapolis

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