Find Vacation Rentals in Annapolis

We have 1,006 properties to choose from
Anytime
Guests
Anytime
Guests

Popular Annapolis Vacation Rentals

Find the perfect Annapolis vacation rental

House Annapolis
from $244 per night
House ∙ 4 guests ∙ 2 bedrooms

93 m² House

5.0
Outstanding(28 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Details
House Annapolis
from $1,954 per night
House ∙ 14 guests ∙ 6 bedrooms

771 m² House

5.0
Outstanding(39 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Details
House Annapolis
from $482 per night
House ∙ 8 guests ∙ 4 bedrooms

204 m² House

5.0
Outstanding(161 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Details
House Annapolis
from $231 per night
5 guests ∙ 3 bedrooms

House

5.0
Outstanding(47 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Details
House Annapolis
from $265 per night
House ∙ 10 guests ∙ 5 bedrooms

223 m² House

4.9
Outstanding(206 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Details
House Annapolis
from $653 per night
House ∙ 14 guests ∙ 5 bedrooms

307 m² House

4.8
Outstanding(38 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Details
House Annapolis
from $353 per night
House ∙ 6 guests ∙ 3 bedrooms

102 m² House

4.9
Outstanding(40 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Details
House Annapolis
from $169 per night
8 guests ∙ 4 bedrooms

House

4.9
Outstanding(15 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Details
House Annapolis
from $774 per night
House ∙ 18 guests ∙ 6 bedrooms

251 m² House

5.0
Outstanding(17 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Details
Show more

Vacation rentals and apartments with air conditioning

House  Annapolis
from $294 per night
6 guests ∙ 3 bedrooms

House

5.0
Outstanding(159 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
Details
House  Annapolis
from $553 per night
House ∙ 5 guests ∙ 2 bedrooms

102 m² House

5.0
Outstanding(188 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
Details
House  Annapolis
from $476 per night
House ∙ 9 guests ∙ 3 bedrooms

112 m² House

Annapolis, Anne Arundel County, Maryland, United States
Air conditioning
Details
Show more

Vacation rentals with Wi-Fi

House  Annapolis
from $1,200 per night
8 guests ∙ 4 bedrooms

House

4.9
Outstanding(5 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Internet
Details
House  Annapolis
from $896 per night
10 guests ∙ 5 bedrooms

House

5.0
Outstanding(42 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Internet
Details
Apartment  Annapolis
from $177 per night
2 guests ∙ 1 bedroom

Apartment

5.0
Outstanding(16 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Internet
Details
Show more

Vacation homes and rentals with a yard

House  Annapolis
from $369 per night
House ∙ 6 guests ∙ 3 bedrooms

167 m² House

4.9
Outstanding(83 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Yard
Details
House  Annapolis
from $1,489 per night
House ∙ 8 guests ∙ 4 bedrooms

279 m² House

5.0
Outstanding(25 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Yard
Details
House  Annapolis
from $449 per night
House ∙ 10 guests ∙ 4 bedrooms

251 m² House

5.0
Outstanding(71 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Yard
Details
Show more

Frequently Asked Questions

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

Accommodation in Annapolis cost from $169 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 1,006 offers in Annapolis.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

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

What are the trendiest neighborhoods in Annapolis?

image-tag