Find Vacation Rentals in Annapolis

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Popular Annapolis Vacation Rentals

Find the perfect Annapolis vacation rental

House Annapolis
$470 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (3 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Vrbo
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House Annapolis
$392 per night
House ∙ 13 guests ∙ 5 bedrooms
4.3
Very good (33 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Details
Vrbo
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House Annapolis
$326 per night
House ∙ 19 guests ∙ 5 bedrooms
5.0
Outstanding (10 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Details
Vrbo
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House Annapolis
$72 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (1 rating)
Annapolis, Anne Arundel County, Maryland, United States
Details
Vrbo
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House Annapolis
$404 per night
House ∙ 14 guests ∙ 4 bedrooms
4.9
Outstanding (36 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Details
Vrbo
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House Annapolis
$635 per night
House ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding (8 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Details
Vrbo
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House Annapolis
$419 per night
House ∙ 12 guests ∙ 6 bedrooms
4.8
Outstanding (5 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Details
Vrbo
Details
Details
Cottage Annapolis
$182 per night
Cottage ∙ 4 guests ∙ 1 bedroom
5.0
Outstanding (263 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Details
Vrbo
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Apartment Annapolis
$158 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding (13 ratings)
Annapolis, Anne Arundel County, Maryland, United States
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Vrbo
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Vacation rentals and apartments with air conditioning

House  Annapolis
$461 per night
House ∙ 14 guests ∙ 4 bedrooms
4.8
Outstanding (54 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
Details
Vrbo
Details
Details
House  Annapolis
$397 per night
House ∙ 12 guests ∙ 4 bedrooms
4.7
Excellent (14 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
Details
Vrbo
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Details
House  Annapolis
$161 per night
House ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding (70 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
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Vrbo
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Vacation rentals with Wi-Fi

House  Annapolis
$272 per night
House ∙ 7 guests ∙ 3 bedrooms
4.8
Outstanding (4 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Internet
Details
Vrbo
Details
Details
House  Annapolis
$683 per night
House ∙ 14 guests ∙ 6 bedrooms
5.0
Outstanding (33 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Internet
Details
Vrbo
Details
Details
House  Annapolis
$272 per night
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding (31 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Internet
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Vrbo
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Apartments and vacation rentals with a kitchen

House  Annapolis
$225 per night
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding (6 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Kitchen
Details
Vrbo
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Details
House  Annapolis
$279 per night
House ∙ 5 guests ∙ 2 bedrooms
4.9
Outstanding (61 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Kitchen
Details
Vrbo
Details
Details
House  Annapolis
$258 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (18 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Kitchen
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Vrbo
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Frequently Asked Questions

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

Accommodation in Annapolis cost from $72 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 910 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.

Popular Day Trips Near Annapolis

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