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308 Annapolis Holiday Rentals

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Compare Annapolis holiday rentals from 6 rental sites including HomeAway, Expedia, TripAdvisor and more, from $63 a night.

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.

Vacation Rentals in Annapolis

Looking for a vacation rental in Annapolis? Tripping.com has 308 vacation rental homes available in Annapolis. You'll find 1 studios, 68 1-bedroom, 58 2-bedroom and 181 rentals with 3 or more bedrooms ranging from $63 a night. For extra convenience, many of these vacation homes can be booked directly online.

The average price of a nightly rental in Annapolis is $553 while the average price of a weekly rental is $25. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Annapolis home is $25.

Wondering if you can bring your dog or cat along with you? There are 76 pet-friendly vacation rentals available in Annapolis. In addition to accommodating pets, Annapolis rentals offer a variety of amenities. In particular, 173 rentals have Internet and WiFi, 263 have TV and/or cable and 40 have a pool or hot tub.

Search properties from 6 vacation rental sites in Annapolis where the top providers in that area are HomeAway, Expedia, and TripAdvisor. There are 259 HomeAway rentals, 15 Expedia short term rentals and 14 TripAdvisor vacation rentals.