Annapolis holiday homes

We found 737 holiday rentals — enter your dates for availability

Select from 422 houses, 59 apartments and other holiday rentals to find the perfect place for your stay in Annapolis. Whether you’re travelling with friends, family or even pets, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a washer and dryer. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

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

Historical Annapolis will entice you

The area's history and live music are just some of the reasons to come on holiday to 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

Do you want to find attractions to see in the area? Venture out of your holiday home and check out everything that makes Annapolis a fun place to get away to. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • U.S. Naval Academy Golf Club (1.9 mi / 3.1 km)
  • Maryland Renaissance Festival (5.4 mi / 8.6 km)
  • Renditions Golf Club (10.7 mi / 17.3 km)
  • Lake Presidential Golf Club (15.7 mi / 25.3 km)
  • Six Flags America (16 mi / 25.7 km)
  • Queenstown Harbor Golf Club (17.4 mi / 28 km)

Exploring the natural landscape of Annapolis

Whether you're looking for adventure or just want to spend some time taking in the scenery, Annapolis is a great place to spend some time outside. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Maryland Quiet Waters Park (2.4 mi / 3.9 km)
  • Bay Ridge Beach (2.9 mi / 4.6 km)
  • Sandy Point Beach (5.7 mi / 9.2 km)
  • Shadyside Park (9.2 mi / 14.8 km)
  • Fort Smallwood Park (11 mi / 17.6 km)
  • Allen Pond Park (13.4 mi / 21.5 km)

Transport to and around Annapolis

Fly into Fort Meade, MD (FME-Tipton), the closest airport, located 16.2 mi (26.1 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Baltimore Washington International 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 holiday home?
Historic District is one of the more popular neighbourhoods to secure a holiday 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 holiday home accommodation in Annapolis?
Houses are the most popular kind of holiday home in Annapolis, according to our data. Even if you have something different in mind, Bookabach has holiday 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 holiday home in Annapolis?
Property type, length of stay and season are some things that can influence the price of a holiday home. Simply enter your travel dates to find your perfect escape. From cosy country cottages to sprawling villas, all Bookabach holiday homes offer unbeatable value.
How much does it cost to rent a beach house in Annapolis?
The average price for a holiday home 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 Bookabach 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 holiday homes 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 holiday homes on Bookabach. 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 holiday homes and every day will be a pool day. Simply enter your travel dates into Bookabach, then use the “pool” filter to find the perfect place to make a splash!
What are popular home amenities in Annapolis?
An electric car charging station, a firepit and an ocean view head the list of most popular home amenities in Annapolis. Whether you’re taking to the road by yourself, with your sweetheart or a bunch of friends, Bookabach will help you find a holiday home that suits your style with a load of extras you’ll love.
Are there large group holiday homes in Annapolis?
Choose from 49 properties in Annapolis that can host a group of 10 or more guests. Whether you’re organising a family trip or some kind of special event, there’s plenty of space to get your favourite people together under the same roof.
Are there holiday homes in Annapolis that welcome kids?
Bring the entire family together for fun-filled adventures in Annapolis at one of our 254 family-friendly holiday 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 favourite.
What are the top attractions for families in Annapolis?
Keeping the kids happy during your holiday in Annapolis is a cinch with these family-friendly attractions:

  • Annapolis Maritime Museum
  • Sandy Point Beach
  • Triton Beach

Are there one-bedroom holiday homes in Annapolis?
Yes, you can pick from 38 one-bedroom homes in Annapolis. Whether you’d like a comfy cottage or a cabin, Bookabach’s one-bedroom homes 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 holiday homes in Annapolis?
Pick from 56 two-bedroom homes 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.
Are there holiday homes with WiFi in Annapolis?
You can choose from 106 holiday homes with WiFi in Annapolis. If you’d like to disconnect from daily life during your escape, but still need to be connected to the web, these getaways have what you need. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in Annapolis?
Pick your dates and then make use of our filters to search for holiday homes with ac in Annapolis on Bookabach. With 246 air-conditioned properties on offer here, you can enjoy a comfortable and cool stay.
How old do you have to be to rent a holiday home in Annapolis?
We recommend you check with the Annapolis holiday home you’d like on Bookabach as age restrictions differ. However, it’s typically 16, 18 or 21.
How long can I rent a holiday home in Annapolis for?
It all depends on the Annapolis property. To browse a list of options offering extended stays, just type your travel dates and guest number into Bookabach’s search page. Look forward to having the property to yourself, along with amenities such as a fully-equipped kitchen and outdoor spaces where the kids can play. Keep an eye out for long-term stays that offer weekly or monthly discounts.

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