Destination guide

Explore the waterfront setting in Annapolis

Enjoy the area's history, live music and art galleries and make a vacation rental your home during your stay in Annapolis. This city's university setting, shopping and boating draw many visitors. Maryland State House and William Paca House are just a couple of the must-sees. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.


Activities and attractions in Annapolis

Are you searching for top things to see and do during your stay? Venture out of your cozy vacation rental and experience everything that makes Annapolis a fun place to get away. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Six Flags America (15.8 mi / 25.5 km)
  • U.S. Naval Academy Golf Club (1.9 mi / 3.1 km)
  • Bowie Golf and Country Club (14.4 mi / 23.1 km)
  • Lake Presidential Golf Club (15.7 mi / 25.3 km)
  • Queenstown Harbor Golf Club (17.4 mi / 28 km)
  • Rocky Point Golf Course (19.2 mi / 30.9 km)
Natural features

Exploring the natural landscape of Annapolis

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Annapolis is a great spot to appreciate mother nature. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • Maryland Quiet Waters Park (2.9 mi / 4.6 km)
  • Sandy Point State Park (5.4 mi / 8.8 km)
  • Shadyside Park (9.2 mi / 14.8 km)
  • Kent Island (9.7 mi / 15.6 km)
  • Allen Pond Park (13.6 mi / 21.9 km)
  • Ferry Park (16.7 mi / 27 km)
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?

Our 2020 vacation rental listings offer a large selection of 484 house rentals around Annapolis. From 326 Houses to 80 Condos/Apartments, find unique vacation rental for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Annapolis is on HomeAway.

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

Whether you're travelling 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:

  • Eastport: 146 vacation rentals
  • Historic District: 91 vacation rentals
  • West Annapolis: 32 vacation rentals
  • Epping Forest: 17 vacation rentals
  • Wardour: 121 vacation rentals

For other neighbourhoods, 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 travelling to Annapolis?

HomeAway offers a large selection of lodging choices 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: 571 home rentals
  • Chase-Lloyd House: 581 home rentals
  • Sandy Point State Park: 559 home rentals
  • Helen Avalynne Tawes Garden: 571 home rentals
  • Maryland Federation of Art: 618 home 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 326 Houses in Annapolis. Our other popular types of vacation rentals in Annapolis include:

  • Condos/Apartments: 80 lodging choices
  • Cottages: 16 lodging choices
  • Bungalows: 16 lodging choices

But you can also enjoy a great stay in one of our other vacation homes 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 96 vacation homes with pool available in Annapolis.

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