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.

Top 15 Recommended vacation rentals in Annapolis
Find your perfect vacation rental in Annapolis from just $107 per night!
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Best Vacation Home Deals in Annapolis
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Popular Rental Amenities in Annapolis
In Annapolis, there are many options if you want to book a an accommodation that allows pets. Hotel room are the most pet-friendly accommodation type in Annapolis. Additionally, a night in a pet-friendly accommodation there is, on average, $538. You can also search for pet-friendly rentals that are centrally located. In Annapolis, One-third of the accommodations vacation rentals less than 2 miles away from the city center.
Waterfront Vacation Rentals in Annapolis

Price and Availability Index in Annapolis
Vacation Rental Price Information in Annapolis
This graph displays the average prices of vacation rentals and apartments located in Annapolis. The week with the highest average prices is in May (5/17 – 5/24). During this week, a nightly price on average will be $658. Vacation rental prices go down to $585 per night in April (4/19 – 4/26).
Rental availability information in Annapolis
Have a look at the above graph to see the average availability of vacation rentals in Annapolis. The busiest time to book a rental in Annapolis so far is in April (4/4 – 4/11), where only 12% rentals are available. July (7/19 – 7/26) has got the highest percentage of available rentals.
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.
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.
Information about vacation rentals in Annapolis
🏡 Vacation rentals available | 1,396 rentals |
---|---|
💳 Possible discounts | up to 51% |
🌙 Nightly prices starting at | $107 |
⭐ Popular amenities | Pets allowed, Pool and Internet |
🐾 Pet friendly homes | 473 homes |
🏊 Vacation rentals with pools | 209 homes |
Frequently Asked Questions
What is the typical nightly price for a vacation home in Annapolis?
The average accommodation in Annapolis is priced at $107 per night. $815 is the average nightly price for house rentals in Annapolis. Apartment rentals in Annapolis cost on average $419 per night.
How many vacation homes are available to book in Annapolis?
There are currently 1,396 vacation rentals in Annapolis to browse and book for your upcoming trip.
What amenities are most popular for vacation rentals in Annapolis?
Travelers look for Pool, Pets allowed, and Internet when booking a vacation rental in Annapolis.
How many vacation rentals with pools are there in Annapolis?
Browse 209 vacation rentals available in Annapolis.
Are pets allowed in vacation homes in Annapolis?
Absolutely, currently there are 473 vacation rentals in Annapolis that allow dogs and the average nightly price is $538.
What's the best time to travel to Annapolis?
If you are booking a vacation rental in Annapolis, consider that rainy season is usually in January or May, with September often being the driest.
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