Annapolis vacation rentals

We found 260 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Annapolis to find one that's perfect for your trip. Vacation homes offer the best amenities for your family, friends, or furry companion, such as parking and a fireplace. At the end of the day, you'll be sure to find a rental that has what everyone needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Annapolis

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Find out more about Annapolis

Choose a vacation rental for your Annapolis getaway

Experience the unique character of Annapolis with a stay in a vacation home rental. You'll find plenty to explore during your stay in the area. If you're looking for accommodations with space to entertain friends and family, Vrbo 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 hoping to find attractions to visit in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Annapolis a one-of-a-kind vacation spot. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • 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 an active traveler or just want to spend some time taking in the scenery, Annapolis is a great spot to appreciate mother nature. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • 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)

Traveling 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 center.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Annapolis?
The most popular types of vacation rentals in Annapolis are bed & breakfasts. Hoping for something different? Vrbo has plenty of options to match our guests' unique needs, so you'll see vacation homes in loads of shapes and sizes. The ideal home away from home is waiting for you --- grab yours today.
How much does it cost to rent a vacation rental in Annapolis?
The average price for a vacation home in Annapolis is based on several factors, including time of year, length of stay and property type. Whether you're looking for a sprawling house with room for friends and family or a comfy cabin just for the two of you, just enter your dates of travel to discover some great-value stays.
How much does it cost to rent a beach house in Annapolis?
When you travel and the style and size of the property will influence the cost of your beachside vacation rental. Click on your Annapolis travel dates to see your options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use our filters to select the features and amenities you want in your rental.
Are there pet-friendly vacation rentals in Annapolis?
With three vacation rentals that host pets, your furry little friend can join in the fun on your Annapolis vacation. Use our filter tool to browse our pet-friendly vacation rentals and find your pawfect pad on Vrbo.
What are popular rental amenities in Annapolis?
A chef, a nearby river and a fireplace top the list of most popular rental amenities in Annapolis. Whether you're taking a trip on your own, with your sweetheart or as a family group, Vrbo will help you find a vacation rental that matches your tastes with all the features you need.
Are there large group vacation rentals in Annapolis?
Yes, you can pick from one of two vacation homes in Annapolis that can accommodate five or more guests. From family getaways to events like a friend's birthday, these stays have ample space to chill out with your favorite people.
Are there vacation rentals in Annapolis that welcome kids?
Annapolis has three family-friendly vacation homes to choose from. And securing a stay that welcomes kiddos is super easy with our "Properties good for families" filter. On top of having the whole place to yourselves, you'll have access to conveniences and perks such as dining rooms, yards and private pools.
Are there vacation rentals with WiFi in Annapolis?
Annapolis has two vacation rentals with WiFi, so you can stay connected while on vacation. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with the family to sending emails, these Vrbo homes make it a cinch to get online.
How old do you have to be to rent a vacation rental in Annapolis?
We recommend checking with the Annapolis vacation property you'd like on Vrbo as the age limit varies. However, it's generally 16, 18 or 21.
How long can I rent a vacation rental in Annapolis for?
The amount of time you can stay in an Annapolis vacation home for is up to each property. Just put in your preferred travel dates to see available options offering longer term stays. They have all you require to make your extended getaway more comfortable and enjoyable, such as laundries and air conditioning. Some Vrbo vacation homes may also offer weekly or monthly discounts, so you can hang around longer for less.
Does Vrbo offer discounts for vacation homes in Annapolis?
On Vrbo, you'll find great discounts and deals for Annapolis. Take a look at our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you're off on a weekend getaway or a much longer stay, Vrbo offers lots of options for every style and budget.

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