Annapolis holiday rentals

We found 259 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Annapolis to find one that's perfect for your trip. Holiday homes provide the amenities that you need and want for you and your friends, family or even pets, such as parking and air conditioning. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Annapolis

Showing deals for:3 Oct - 10 Oct
  • 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

Choose a holiday rental for your Annapolis getaway

Learn about the unique charm of Annapolis with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around Annapolis

Are you searching for attractions to see in the city? Venture out of your holiday home and check out everything that Annapolis has to offer. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Sea Ranch Golf Links (8.3 mi / 13.4 km)
  • Fort Ross Vineyard (17.5 mi / 28.2 km)
  • Flowers Vineyard and Winery (13.7 mi / 22.1 km)
  • Maple Creek Winery (14.8 mi / 23.8 km)
  • Yorkville Cellars (14.8 mi / 23.9 km)
  • Albertina Wine Cellar (19.2 mi / 30.8 km)

Exploring the natural features in Annapolis

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Annapolis. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Pebble Beach (4.2 mi / 6.7 km)
  • Black Point Beach (4.3 mi / 6.9 km)
  • Gualala River (6 mi / 9.7 km)
  • Ocean Cove (11.8 mi / 19 km)
  • Stillwater Cove Regional Park (12.6 mi / 20.3 km)
  • Lake Sonoma (18.7 mi / 30.1 km)

Travelling to and around Annapolis

The nearest airport is in Santa Rosa, CA (STS-Sonoma County), located 33.6 mi (54.1 km) from the city centre.

Frequently asked questions

What is the most popular type of holiday home accommodation in Annapolis?
The most sought-after types of holiday homes in Annapolis are houses. Hoping for something different? Stayz has numerous options to match the diverse needs of our guests, so you'll see holiday properties in all sizes and shapes. The ideal fit is waiting for you --- find yours today.
How much does it cost to rent a holiday home in Annapolis?
A range of factors can influence how much you pay for a holiday home in Annapolis, like the type of property, season and length of stay. But, all Stayz homes have something in common --- exceptional value. Just add your travel dates to find your ideal match.
How much does it cost to rent a beach house in Annapolis?
When you travel and the size and style of the property will influence the cost of your beachside holiday home. Click on your Annapolis travel dates to see all your options on Stayz. Did someone just say "private pool"? Use the filters to choose the features and amenities you want in your holiday home.
Are there pet-friendly holiday homes in Annapolis?
Pack a suitcase for your pup because Annapolis has two holiday homes that welcome pets with open arms. Let your furriest pal enjoy the family fun at one of our pet-friendly holiday homes on Stayz. Simply enter your travel dates and destination, then check the "Pets allowed" filter box.
What are popular home amenities in Annapolis?
The most popular home amenities people are looking for in Annapolis are a firepit, a fireplace and a nearby river. Whether you're travelling with family, pals or even pets, Stayz holiday homes feature the best amenities for beginning new traditions with the people you love.
Are there holiday homes in Annapolis that welcome kids?
Annapolis has two family-friendly holiday homes to pick from. And finding a stay that welcomes kiddos is easy with our "Properties good for families" filter. In addition to having the entire place to yourselves, you'll also enjoy access to perks and amenities such as dining rooms, pools and kitchens.
What are the top attractions for families in Annapolis?
Keeping the kids amused during your holiday in Annapolis is a snap with these leading family-friendly attractions:

  • Hauser Bridge
  • Kruse Rhododendron State Natural Reserve
  • Fisk Mill Cove

How old do you have to be to rent a holiday home in Annapolis?
You should check with the Annapolis holiday property you're considering on Stayz as the age limit varies. 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, simply type your dates and number of people into the Stayz search page. Look forward to having the whole property to yourself, along with home comforts such as air conditioning, a kitchen and a yard where the kids can run and play. Be on the lookout for any long-term stays that offer discounted weekly or monthly prices.

More Holiday Rentals ideas

People also search for