Annapolis holiday rentals

We found 20 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 11 cabins and other holiday rentals in Annapolis that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, such as parking and air conditioning. At the end of the day, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Travel to relaxing Annapolis

The riverfront and parks create a pretty picture of Annapolis. Travellers appreciate the restaurants in this relaxing city. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Exploring the natural landscape of Annapolis

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

  • Taum Sauk Mountain State Park (14.6 mi / 23.5 km)
  • Johnson's Shut-ins State Park (16.7 mi / 26.9 km)
  • Elephant Rocks State Park (20.5 mi / 33 km)
  • K Bridge Recreation Area (4.2 mi / 6.7 km)
  • Clearwater Lake (15.7 mi / 25.3 km)
  • Walnut Hollow Lake (2 mi / 3.3 km)

Frequently asked questions

How much does it cost to rent a holiday home in Annapolis?

The average price for a holiday home in Annapolis can vary based on factors including length of stay, season and property type. Whether you'd like a sprawling villa with space for extended family or an apartment for you and your other half, just add your travel dates to find stays with great value.

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

Prices for beach houses in Annapolis may differ depending on the type and size of the property and when you're travelling. All you need to do is enter your travel dates into Stayz and how many guests to view available options and prices. From there you can use our filter tool to tailor your search results by ratings, nearby activities and more.

What are the top attractions for families in Annapolis?

Keeping the kids amused during your holiday in Annapolis is simple with these top family-friendly attractions:

  • Crane Lake Recreation Area
  • Walnut Hollow Lake
  • K Bridge Recreation Area

How old do you have to be to rent a holiday home in Annapolis?

We recommend you check with the Annapolis holiday home you're looking at on Stayz as the age limit differs. However, typically it's 16, 18 or 21.

How long can I rent a holiday home in Annapolis for?

It really depends on the Annapolis property. To view a list of options offering extended stays, just enter your dates and guest number into the Stayz search page. Enjoy having the property to yourself, along with home comforts such as a fully-equipped kitchen and outdoor spaces to play in. Keep an eye out for any long-term stays that offer weekly or monthly discounts.

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