Skip to content

Annapolis vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Annapolis

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Superhost
Home in Annapolis
Cozy 2br home w/ parking in downtown Annapolis
Ideally located in the heart of downtown Annapolis's Historic & Art Districts. Detached home with historic charm & an inviting front porch, 1 car parking included. Open floor plan to include a living room (with queen sleeper sofa), workspace, 1/2 bath & eat in kitchen on the 1st floor. 2 bedrooms and a full bath upstairs. Enclosed rear yard provides an opportunity to create a lovely quiet space out our back door. A perfect location for C-Week, Boat Shows & other festivals in Historic Annapolis.
$133 per night
Superhost
Guesthouse in Annapolis
Calico Cottage Guest House, king bed, free parking
Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.
$89 per night
Superhost
Guesthouse in Annapolis
RECENTLY RENOVATED Cottage Near Downtown Annapolis
Recently renovated (Feb. 2021) one bedroom Guesthouse with fully equipped kitchen, new king sized bed with premium Saatva mattress, full bathroom and large living room in a quiet neighborhood near the South River, Quiet Waters Park and downtown historic Annapolis. We employ professional cleaning services between each guest stay.
$105 per night

Stay near Annapolis's top sights

Annapolis City Dock34 locals recommend
Navy-Marine Corps Memorial Stadium34 locals recommend
Boatyard Bar & Grill127 locals recommend
Iron Rooster - Annapolis104 locals recommend
Blackwall Hitch59 locals recommend
Chick & Ruth's Delly60 locals recommend

Annapolis home rentals

Superhost
Home in Annapolis
New Hotel Chic
$240 per night
Superhost
Home in Annapolis
Cape St Claire waterfront getaway
$135 per night
Superhost
Home in Pasadena
Sea Dreamer aka Phenomenal Hospitality
$87 per night
Superhost
Home in Annapolis
Historic Downtown in-law suite
$131 per night
Superhost
Home in Annapolis
Elegant & Authentic Annapolis
$187 per night
Superhost
Home in Annapolis
Historic Home w/ Parking Steps From Capital & USNA
$243 per night
Superhost
Home in Annapolis
House Steps to Downtown/Main St
$117 per night
Superhost
Home in Annapolis
Blocks to Main St, Walk-up Rowhouse
$116 per night
Superhost
Home in Annapolis
Restful and Charming Home in Eastport
$198 per night
Superhost
Home in Annapolis
Naptown Suite
$115 per night
Superhost
Home in Edgewater
Relaxing Turkey Point Retreat-Steps to the marina!
$81 per night
Superhost
Home in Annapolis
Green On Fleet - Rowhouse in Historic Annapolis
$254 per night

Your guide to Annapolis

All About Annapolis

The capital of Maryland, Annapolis sits on the banks of Chesapeake Bay and is known for its historic neighborhoods and 18th-century Colonial, Georgian, and Victorian homes. With its reputation as the sailing capital of the United States, and home to the U.S. Naval Academy, Annapolis holds several significant historical credentials, including a founding that dates back to 1649. St. John's College, one of the oldest universities in the country, still stands proud on Annapolis soil.

Today, this prosperous East Coast city is known more for its thriving downtown Historic District with boutique shops, galleries, and architectural sites that provide a day of exploration before heading to the Eastport District, where the Annapolis culinary scene emphasizes locally sourced oysters, crabs, and scallops. For nightlife, West Street is where you will find several bars, clubs, and restaurants, many of which regularly host live music on the weekends.


The best time to stay in a vacation rental in Annapolis

Annapolis experiences drastic weather changes from season to season. The summer months tend to be hot and humid, with moderate precipitation and long pleasant nights. Several festivals occur during the summer days, like a Renaissance fair in a fictional 16th-century village with costumed events, vendors, and medieval-era arts and crafts. Or the weekly Wednesday Night Sailboat Races that take place from May through September.

The winter sees temperatures drop to below freezing with an occasional dusting of snow. However, Annapolis’ warm cafes and cozy street-side restaurants can make brisk days feel quite pleasant. The shoulder seasons are an excellent time to look for vacation rentals in Annapolis, as the spring weather conditions that are temperate also mark the beginning of the sailing season. The fall hosts a brilliant display of autumn hues in the treetops throughout the city with similar weather patterns to that of spring.


Top things to do in Annapolis

Annapolis Maritime Museum

This waterfront museum houses several exhibitions and displays that detail the area's maritime history and the ocean's significance in its economic, social, and cultural developments. Exhibits explain Chesapeake Bay’s unique ecological makeup and how it has impacted the fishing industry over the years. In addition, several art and photography displays highlight the region's social makeup through contributions by local and internationally renowned artists.

Historic London Town

Located just outside of Annapolis in the town of Edgewater, this 23-acre park is a recreation of a lost 18th-century colonial village that would have been common in the area at the time. A carpenter's shop, mayor's tenement, picnic areas, and ten acres of woodland and ornamental gardens are all waiting to be explored in the area. Recreated through a series of archeological discoveries, most of the buildings are full of everyday objects that would have been found and used at the time.

Lake Waterford Park

This 108-acre park is where the locals come to stretch out when the weather is nice. It includes a full lineup of recreational activities, from tennis courts to football fields. Walking trails and hiking paths meander through much of the wooded park, and there’s a 12-acre lake for spotting waterfowl and fishing from the shores.

Destinations to explore