Annapolis vacation rentals

We found 702 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
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Select from 409 houses, 55 apartments, and other vacation rentals to find the perfect place for your stay in Annapolis. Whether you're traveling with family, friends, or just your furry companion, vacation rentals have the best amenities for hanging out with the people that matter most, which might include a garden and pool. You'll be sure to find a rental that has what everyone needs, including options that are accessible or non-smoking.

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Historic Annapolis will entice you

The area's history and live music are just a few of the reasons to vacation in Annapolis. Renowned for its university setting, shopping and restaurants, this city welcomes all visitors. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Annapolis

Are you searching for things to do while you're in town? Venture out of your cozy vacation rental and check out everything that makes Annapolis a one-of-a-kind vacation spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Six Flags America (16 mi / 25.7 km)
  • Queenstown Harbor Golf Club (17.4 mi / 28 km)
  • St. Michaels Winery (19.9 mi / 32.1 km)
  • Chesapeake Beach Water Park (19.9 mi / 32.1 km)
  • Laurel Park (20.3 mi / 32.7 km)
  • Thurgood Marshall Memorial (0.1 mi / 0.1 km)

Exploring the natural landscape of Annapolis

Whether you're an active traveler or just want to appreciate the scenery, Annapolis is a great place to get out in nature. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Maryland Quiet Waters Park (2.4 mi / 3.9 km)
  • Sandy Point State Park (5.4 mi / 8.8 km)
  • Sandy Point Beach (5.7 mi / 9.2 km)
  • Rocky Point Park and Beach (19.5 mi / 31.3 km)
  • BWI Trail (20.5 mi / 33 km)
  • Patuxent River (20.7 mi / 33.3 km)

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 can't find a flight that's convenient for your trip, you might consider flying into Baltimore Washington Intl. Airport (BWI), which is 16.8 mi (27 km) away.

Frequently asked questions

What is the best area to stay in Annapolis when booking a vacation rental?

Historic District is one of the more popular neighborhoods to secure a vacation property in Annapolis. During your stay, don't miss big-hitting attractions like Maryland State House and William Paca House.

What is the most popular type of vacation rental accommodation in Annapolis?

Houses are the most popular kind of vacation rental in Annapolis, according to our data. Even if you have something different in mind, Vrbo has vacation homes in all sizes and shapes. Take a look at our options to find your perfect match.

How much does it cost to rent a vacation rental in Annapolis?

Property type, length of stay and season are some things that can influence the price of a vacation home. Simply enter your travel dates to find your perfect escape. From cozy country cottages to sprawling villas, all Vrbo vacation rentals offer unbeatable value.

How much does it cost to rent a beach house in Annapolis?

The average price for a vacation rental near the beach in Annapolis depends on when you're going and the style and size of property you're searching for. Find prices easily and quickly on Vrbo by entering your dates of travel. Then use our filters to choose the number of bedrooms and amenities that you prefer, such as WiFi, a pool and air conditioning.

Are there pet-friendly vacation rentals in Annapolis?

Pack a squeezy toy and a bone for your pup because Annapolis has 256 stays that roll out the welcome mat to doggie guests. Let your four-legged buddy join in with the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates then check the "Pets allowed" filter box.

Can I rent a house with a pool in Annapolis?

Pack your swimwear and swim ring, because there are 27 houses with a private pool in Annapolis. Stay at one of these terrific vacation homes and every day will be a pool day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find the perfect place to make a splash!

What are popular rental amenities in Annapolis?

An electric car charging station, a firepit and an ocean view head the list of most popular rental amenities in Annapolis. Whether you're taking to the road by yourself, with your sweetheart or a bunch of friends, Vrbo will help you find a vacation home that suits your style with a load of extras you'll love.

Are there large group vacation rentals in Annapolis?

Choose from 49 properties in Annapolis that can host a group of 10 or more guests. Whether you're organizing a family trip or some kind of special event, there's plenty of space to get your favorite people together under the same roof.

Are there vacation rentals in Annapolis that welcome kids?

Bring the entire family together for fun-filled adventures in Annapolis at one of our 254 family-friendly vacation homes. These stays provide conveniences that are suitable for getaways with the little ones, like laundries, multiple bedrooms and outdoor spaces. Simply check the "Properties good for families" filter and book your favorite.

What are the top attractions for families in Annapolis?

Keeping the kids happy during your vacation in Annapolis is a cinch with these family-friendly attractions:

  • Annapolis Maritime Museum
  • Sandy Point Beach
  • Triton Beach

Are there one-bedroom vacation rentals in Annapolis?

Yes, you can pick from 38 one-bedroom rentals in Annapolis. Whether you'd like a comfy cottage or a cabin, Vrbo's one-bedroom rentals are just right if you don't need lots of room. One of the major perks of having your own place? You won't ever have to share your trip with strangers.

Can I find two-bedroom vacation rentals in Annapolis?

Pick from 56 two-bedroom rentals in Annapolis. Put the kids in the second room or maybe fill it with a couple of your best buddies. There's a comfy spot for whoever's fortunate enough to be coming along.

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