Best Vacation Home Deals in Annapolis
Discover a vacation home matching your expectations among the 871 great options from more than 18 providers in Annapolis. By comparing these properties, HomeToGo features the best deals as well as the highest rated properties in Annapolis.
Recommended Vacation Rentals in Annapolis
Find your perfect vacation rental in Annapolis: from $33 per night
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Popular Rental Amenities in Annapolis
Price and Availability Index in Annapolis
Vacation Rental Price Information in Annapolis
The price graph will give you the nightly price average for the upcoming months of the year. Annapolis is more expensive in October (10/19 - 10/26), where prices are on average $431 a night. The week with the lowest average prices is in May (5/18 - 5/25).
Rental Availability Information in Annapolis
This graph shows the vacation rental availability rate for the next twelve months. Be careful if you plan to go to Annapolis in May, as it comprises the busiest week of the next 12 months (5/18 - 5/25). May (5/11 - 5/18) has got the highest percentage of available rentals.
The Weather in Annapolis
Check out our climate diagram to find the perfect month for your vacation. In July maximum temperatures go higher than 86°. However, temperatures can go lower than 30° in Annapolis in January. The rainiest month is July while the driest month is September.
Dive into the past with an Annapolis vacation rental
Whether they’re colonial cottages or modern condos, vacation rentals in Annapolis are close to the action of this historic yet bustling modern city. With all the comforts of home combined with exciting things to see and do, this scenic area of Maryland will have you returning again and again.
Art, history, and culture
From its earliest days, Annapolis has been known as the “Athens of America” for its cultural, social and intellectual activities. Your vacation rental in Annapolis will be close to many artistic and cultural offerings, such as Historic London Town and Gardens, where you can explore 23 acres of history, archeology, and beautiful flora.
Experience performances by the Annapolis Shakespeare Company, Ballet Theatre of Maryland, or the Annapolis Symphony Orchestra. If visual art is your cup of tea, there are 25 fine art galleries downtown alone, as well as the Elizabeth Myers Mitchell Gallery, a museum that is open daily and has free admission.
Music and other nightlife
Much of historic Annapolis is walkable. Across the street from the visitors center, in the Arts District, is Rams Head On Stage, a delightful bar/restaurant/concert venue with a healthy offering of music or comedy almost every night. There’s an active music scene in Annapolis, with dozens of local bands calling the area home. See them perform in pubs, bars, and restaurants all over the city, such as Armadillo's Bar and Grill and Castlebay Irish Pub.
Sailing and other excursions
Annapolis is known for its sailing and other water activities on the Chesapeake Bay, and there’s always something to see near the harbor, such as the US Naval Academy Museum. There are many tours in the area, on water and on land, including Colonial Tours of Annapolis, Pirate Adventures on the Chesapeake (great for kids), and Segs in the City.
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