Annapolis, MD, USA

Annapolis, MD, USA

We found 429 vacation rentals — enter your dates for availability


Find the best place to stay — Annapolis

Where to stay near Annapolis, MD?

Our 2018 property listings offer a large selection of 429 vacation rentals near Annapolis. From 291 houses to 33 apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Annapolis for a holiday or a weekend are on HomeAway.

Appealing Annapolis

Annapolis vacation rentals are the perfect base for exploring Maryland’s capital city. Known locally as “America’s sailing capital,” the historic city of Annapolis has much to offer everyone, from families to couples and groups of friends. Whether you’re here for the city’s rich maritime history, to spend time in the great outdoors cycling your way through Sandy Point State Park, to take to the water on a paddleboard in the Chesapeake Bay, or to simply take in the atmosphere downtown, Annapolis is sure to have something to float your boat.

Dive into everything Annapolis has to offer

Annapolis is a rich and diverse city with activities that are sure to please everyone. The historic center will charm you with its array of 18th-century brick houses, and the year-round walking tours of the city are an excellent way of delving deeper into the city’s past. If you’re looking for something sportier, why not take advantage of the city’s access to the Chesapeake Bay? Here, you can enjoy a variety of water sports, including paddleboarding, kayaking, and of course, sailing.

See the sea in Annapolis

Annapolis is known for its maritime history, and where better to learn about this than the United States Naval Academy nearby? U.S. Navy recruits are still trained here, and you can get a glimpse into life on the sea in a guided tour around the facilities. If you’re lucky, sports fans may even be able to catch an event held in the off-campus Navy-Marine Corps Memorial Stadium! If you’re looking to relax and take things at a slower pace, head on over to Ego Alley, where you can sit and enjoy great food and drinks while watching the boats in the harbor.

Keep cool in Annapolis

Annapolis’ location on the Chesapeake Bay and its low elevation on the Atlantic Coastal Plain mean that Annapolis vacation rentals are an ideal accommodation spot all year round. Although the city falls into a subtropical climate zone, its proximity to the water keeps a cool breeze flowing in the summer and helps to keep winter temperatures higher than other states further inland. June through August sees temperature highs of over 80°F, with winters seeing average temperatures of around 30°F. There is higher than average rainfall here because of the climate, so don’t forget to pack your waterproof clothing!

Experience nature in Annapolis

A short drive away from many Annapolis vacation rentals, and out of Downtown Annapolis, lies the 786-acre Sandy Point State Park. Overlooking the Chesapeake Bay, Sandy Point is perfect for activities like wildlife and bird watching. Why not take in the breathtaking vistas while sampling local produce on a beach picnic? Or maybe even hire a boat for some off-shore fishing. This Maryland State Park is also home to the 13-mile Baltimore-Annapolis Trail, which takes riders through woodlands and open spaces, right through to suburban areas. Its largely flat terrain makes it the perfect way for the whole family to enjoy the great outdoors.