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 $196 per night!
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Book a welcoming vacation home from $196 per night by exploring the 1,365 properties being offered in Annapolis. All of the accommodations from our partner websites are directly compared on our website so you can save up to 56%.
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Popular Rental Amenities in Annapolis
Many users pay a closer look at the vacation rentals with a pool. A few of the properties have one in this destination. Additionally, more hotel room provide a pool than condo. Most of the hotel room with pools in Annapolis accommodate 11 guests and have an average cost of $598 per night. Among these accommodations, 58 of them are situated within 2 kilometres of water.
What are the best places to discover the arts and culture of 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.
Where are the unique attractions in Annapolis?
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 | 1,365 rentals |
|---|---|
| 💳 Possible discounts | up to 56% |
| 🌙 Nightly prices starting at | $196 |
| ⭐ Popular amenities | Pool, Pets allowed and Internet |
| 🐾 Pet friendly homes | 470 homes |
| 🏊 Vacation rentals with pools | 205 homes |
128,234 reviews
Annapolis vacation rentals have an average rating of 4.7/5 on 128,234 reviews left by travelers.
Frequently Asked Questions
What is the typical availability of vacation rentals in Annapolis?
We found 1,365 vacation homes in Annapolis available for your next trip.
What are the most popular vacation home amenities in Annapolis?
When looking to book a vacation home in Annapolis, the most requested amenities include Pool, Pets allowed, and Internet.
Are there pet-friendly vacation rentals in Annapolis?
If you're travelling with a dog, over 34% of vacation rentals in Annapolis are pet-friendly.
What's the best month to book a vacation rental in Annapolis?
When booking a vacation rental in Annapolis, remember that the rainiest months are usually January and May, with September often being the sunniest.
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