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Annapolis Vacation Rentals

This section features the following homes, villas, cabins, cottages or condos listed below. Please click on the description to view any of the Annapolis rentals you see listed for more information. Vacation rentals in Annapolis, Maryland are added and updated every week, so please bookmark us and visit again. Be sure to check out Kent Island (9 miles), St Michaels (19 miles), Baltimore (22 miles), Oxford (26 miles), Chestertown (27 miles), and Prince Frederick (30 miles) for additional vacation rental choices. (Notice a problem with our distances? Report it here.)

Photo's available Pets? please inquire Swimming pool Jacuzzi Availability Calendar
Min Rate Max Rate Per Property Type Beds Baths Pets Pool Jacuzzi
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Type Bed Bath Sleeps Rates or Community Property Name
 Cottage 2 1 5 $1550-$1850 USD/wk The Waterside Cottage on Harness Creek
 House 3 3 8 $1500-$2000 USD/wk Annapolis Waterfront South River Chesapeake Bay
 House 3 10 $2500-$5000 USD/wk Downtown Home- Still Available for Commissioning Week!
 House 3 12 $2650-$5500 USD/wk Relax, Entertain, or Walk to Everything Downtown!
 Cottage 4 2 10 $1750-$2500 USD/wk Chesapeake Bay Waterfront Cottage near Annapolis
 House 4 2 10 $850-$1400 USD/wk Spacious home between Annapolis, Baltimore and Washington DC
 House 4 3 10 $2000-$5000 USD/wk Harwood House
 House 5 12 $2100-$3150 USD/wk Woodlore Private Contemporary
Found 8 properties

Annapolis, Maryland Vacation Rentals and Tourism

Vacation rentals in Annapolis, Maryland, offer a vacation home in the city. Comfortable, luxurious Annapolis vacation apartment rentals offer access to the nation’s capitol city with all the amenities vacation rentals offer. Choose from our selection of Annapolis vacation homes, waterfront condo rentals in Annapolis, and Annapolis vacation cottage rentals for a vacation with all the comforts of home, something Annapolis hotels just can’t offer.

Annapolis, MD, rentals are near the Naval Academy, historic Annapolis, and lots of fun things to do. From your Annapolis rental near the Chesapeake Bay, enjoy kayaking, fishing and crabbing. Annapolis vacation rentals are near many restaurants and shops and the monuments and museums in Washington, DC.

The top time to book vacation rentals in Annapolis is summer and fall with vacation values in the late winter. Most Annapolis vacation house rentals are available year round for a family vacation or to visit Annapolis any time of year.

Annapolis, Maryland, vacation rentals are about 30 miles from Washington, DC, and about 30 miles from Baltimore, MD. It’s easy to get to your Annapolis vacation rental by flying into Baltimore Washington International Airport, about 30 minutes from Annapolis rentals available on Vacation Rentals.com.