Discover a selection of 429 vacation rentals in Annapolis, MD that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $110 per night, and houses and cottages are popular options for a stay in Annapolis. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Annapolis
Destination guide

Find history from an oceanfront accommodation in Annapolis

This city, situated along the Chesapeake Bay, serves as the state capital. You can admire the Maryland State House's domed roof and other impressive 18th-century buildings in the city's historic district. You could also stop by the United States Naval Academy for a tour of the campus and to visit the U.S. Naval Academy Museum, where you'll learn about the Navy's history and see models of famous ships. You might stay at a Maryland oceanfront rental in Annapolis that includes a complete kitchen with a full-sized refrigerator and microwave for cooking meals, then eat in the dining room with a lovely view of the ocean.

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.

How many vacation rentals are available around Annapolis, MD?

Our 2021 property listings offer a large selection of 429 vacation rentals around Annapolis. From 344 house rentals to 20 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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: 102 vacation rentals
  • Eastport: 134 vacation rentals
  • Epping Forest: 16 vacation rentals
  • Homewood: 46 vacation rentals
  • Murray Hill: 88 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:

  • Chesapeake Bay Bridge: 541 vacation rentals
  • Annapolis Maritime Museum: 586 vacation rentals
  • 97, 99 and 101 East Street: 563 vacation rentals
  • Navy-Marine Corps Memorial Stadium: 558 vacation rentals
  • Annapolis City Dock: 567 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 344 Houses in Annapolis. Our other popular types of vacation rentals in Annapolis include:

  • Cottages: 20 rentals available
  • Cabins: 21 rentals available
  • Condos/Apartments: 70 rentals available

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

Can I find a vacation rental with pool in Annapolis?

Yes, you can select your preferred vacation rental with pool among our 69 vacation rentals with pool available in Annapolis. Please use our search bar to access the selection of vacation rentals available.