Destination guide

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.

Things to do

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.


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.


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!

Natural features

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.

How to get there

Transportation to and around Annapolis

Fly into Fort Meade, MD (FME-Tipton), the closest airport, located 16.2 mi (26.1 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall), which is 16.8 mi (27 km) away.

Can I find a vacation rental around Annapolis?

Yes, our 2019 property listings offer a large selection of 535 vacation rentals near Annapolis. From 359 Houses to 86 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 HomeAway.

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: 104 vacation rentals
  • Eastport: 158 vacation rentals
  • Arundel on the Bay: 18 vacation rentals
  • Homewood: 60 vacation rentals
  • Naval Academy: 110 vacation rentals

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

What are the popular points of interest near where I can stay when traveling to Annapolis?

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

  • Chesapeake Bay Bridge: 636 vacation rentals
  • Sandy Point State Park: 626 vacation rentals
  • U.S. Naval Academy: 664 vacation rentals
  • Maryland Quiet Waters Park: 686 vacation rentals
  • Navy-Marine Corps Memorial Stadium: 651 vacation rentals

But there are many other points of interest around Annapolis listed on HomeAway 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. HomeAway has 359 Houses in Annapolis. Our other popular types of vacation rentals in Annapolis include:

  • Condos/Apartments: 86 rentals available
  • Cottages: 20 rentals available
  • Bungalows: 20 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 preferred vacation rental with pool among our 98 vacation rentals with pool available in Annapolis. Please use our search bar to access the selection of vacation rentals available.

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