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.
Choose the perfect vacation rental
Best Vacation Home Deals in Annapolis
Discover a vacation home matching your expectations among the 859 great options from more than 7 providers in Annapolis. By comparing these properties, HomeToGo features the best deals as well as the highest rated properties in Annapolis.
Top-Rated Rentals and Accommodations in Annapolis
Recommended Vacation Rentals in Annapolis
Find your perfect vacation rental in Annapolis: from $140 per night
Budget-friendly Vacation Rentals in Annapolis
Vacation rentals with Wi-Fi
Stay connected while traveling and book a Annapolis accommodation with high-speed internet.
Apartments and vacation rentals with a kitchen
Cook up a feast on your next vacation and book a Annapolis rental with full kitchen.
Vacation rentals and apartments with air conditioning
Keep cool during your trip to Annapolis and book a vacation rental with air conditioning.
Popular Rental Amenities in Annapolis
Waterfront Vacation Rentals in Annapolis
Want to find an amazing beach house in Annapolis?
Use the 'distance to water' filter during your search and discover the perfect beach houses for your vacation. There is a variety of home rentals in Annapolis that are just a short walk from the ocean. From pet-friendly homes by the beach to waterfront offers with hot tubs, the dream accommodation in Annapolis awaits - book it now with HomeToGo.
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 January while the driest month is September.
7-Day Weather Forecast in Annapolis
Accommodations for your vacation in Annapolis
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.
Information about vacation rentals in Annapolis
|🏡 Vacation rentals||859 properties|
|💳 Possible discounts||up to 60%|
|🌙 Nightly prices starting at||$140|
|⭐ Popular amenities||Internet, Air conditioning and TV|
|🐾 Pet friendly accommodations||246 properties|
|🏊 Vacation rentals with pools||269 properties|
Frequently Asked Questions
What is the average price per night for a vacation rental in Annapolis?
The average accommodation in Annapolis is priced at $140 per night. If you would like to stay in a house rental, the average price is $877 per night. A apartment rental Annapolis will cost on average $341 per night.
How many vacation homes are available for booking in Annapolis?
Currently there are 859 vacation rentals in Annapolis to choose from and book for your next trip.
What amenities are most popular for vacation homes in Annapolis?
If you're looking to book a vacation rental in Annapolis, others search for accommodation with Internet, Air conditioning and TV.
How many vacation rentals with a pool are there in Annapolis?
There are 269 vacation rentals across 7 providers in Annapolis.
Are dogs allowed in vacation homes in Annapolis?
Yes, there are 246 vacation homes in Annapolis that allow dogs , with an average rate of $561 per night.
What's the best month to travel to Annapolis?
The warmest months in Annapolis are July and August, with temperatures around 86 °F. The coldest months in Annapolis are January and February, with 30 °F on average.
We list offers from thousands of providers, including:
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