0 Bedrooms for 1 Guest
Price $10 - $1000+

353 Annapolis Holiday Rentals, Houses & Apartments

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews. Compare Annapolis holiday rentals from 6 rental sites including HomeAway, Booking.com, TripAdvisor, and more, ranging from $56 to $7000 a night. 
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    Information about Annapolis

    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 the perfect vacation rental for your Annapolis getaway? Tripping.com’s got your trip covered. Whether you’re seeking a villa, cabin or cottage, Annapolis offers 355 affordable homes to choose from, offering far more amenities, space and convenience than the average hotel room. Select from 174 properties with high-speed internet, 38 full with jacuzzi and pool, and NaN homes complete with outdoor patio well-suited for a barbecue with loved ones. Whatever your needs, find the perfect rental that best matches your accommodation style and budget.

    For travelers planning for an extended stay, long-term lodging and corporate rentals only cost an average of $5113 a month. Save hundreds with Tripping.com and even book instantly with properties marked “Instabook.” Annapolis has 355 gorgeous homes with 77 pet-friendly rentals to choose from, perfect for your furry friends. Check out our listings now to get the latest deals, and book the right vacation rental for you and the whole family. Feel at home wherever you are and experience an unforgettable vacation with Tripping.com.

    Search properties from 6 rental sites in Annapolis where the top providers in that area are HomeAway, Booking.com, and TripAdvisor. There are 167 HomeAway rentals, 138 Booking.com short term rentals and 27 TripAdvisor vacation rentals.