Where to stay around Annapolis, MD?

Our 2018 property listings offer a large selection of 516 vacation rentals near Annapolis. From 351 Houses to 75 Condos/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 VRBO.

What is the best area to stay when traveling to Annapolis?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Annapolis:

  • Historic District: 109 vacation rentals
  • Eastport: 148 vacation rentals
  • Bay Ridge: 31 vacation rentals
  • Murray Hill: 98 vacation rentals
  • Arundel on the Bay: 15 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Annapolis?

VRBO offers a large selection of vacation rentals near lovely places in Annapolis. From VRBO travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Sandy Point State Park: 620 vacation rentals
  • Chesapeake Bay Bridge: 628 vacation rentals
  • Maryland Quiet Waters Park: 670 vacation rentals
  • U.S. Naval Academy: 661 vacation rentals
  • Maryland State House: 658 vacation rentals

But there are many other points of interest around Annapolis listed on VRBO where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Annapolis?

Yes, of course. VRBO has 351 Houses in Annapolis. Our other popular types of vacation rentals in Annapolis include:

  • Condos/Apartments: 75 rentals available
  • Studios: 40 rentals available
  • Townhouses: 39 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Cabins and more.

Can I find a vacation rental with pool in Annapolis?

Yes, you can select your prefered vacation rental with pool among our 103 vacation rentals with pool available in Annapolis. Please use our search bar to access the selection of vacation rentals available.

    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.