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314 Annapolis Holiday Rentals

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Compare Annapolis holiday rentals from 6 rental sites including HomeAway, Expedia, Booking.com 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

Save hundreds with a vacation home rental from Tripping.com and forget the hotel room. For the ultimate getaway, Annapolis offers 314 affordable vacation rentals with a price to match your budget and accommodation needs. Prices in Annapolis start at an average price of $499 a night with long-term rentals averaging $25 a month.

These vacation rentals offer a range of amenities, so you’ll feel right at home. For those looking to stay in a corporate rental, 181 of Annapolis’s rentals offer high speed WiFi Internet so you can easily keep in touch with your company or team. Go for a swim at one of the 42 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 270 vacation home rentals.

Traveling with your dog or cat? Choose from 83 pet-friendly rentals in Annapolis that allow you to bring your extended family along.Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your pets. Many properties allow you to book directly online, so once you find that perfect vacation rental, you’ll be all set to go!

Search properties from 6 vacation rental sites in Annapolis where the top providers in that area are HomeAway, Expedia, and Booking.com. There are 266 HomeAway rentals, 15 Expedia short term rentals and 13 Booking.com vacation rentals.