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

392 Annapolis Vacation Rentals & Short Term Rentals

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

    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

    Find the best Annapolis vacation rentals with Tripping.com. Choose from 369 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $50 a night to $7000 a night.

    Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 183 of homes in Annapolis offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 40 rentals with pool or jacuzzi, or relax with the family in one of the 319 homes with cable TV.

    For all those dog lovers and cat lovers, Annapolis offers 81 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

    Search properties from 6 rental sites in Annapolis where the top providers in that area are HomeAway, Booking.com, and TripAdvisor. There are 174 HomeAway rentals, 143 Booking.com short term rentals and 27 TripAdvisor vacation rentals.