Annapolis Vacation Rentals

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Annapolis Travel Guide

Maryland’s charming state capital is a calling your name for your next vacation.

Things to Do in Annapolis

The city sits along the water of the Chesapeake Bay in Eastern Maryland. Wander through the red brick sidewalks of Downtown Annapolis, where you’ll find restaurants offering the catch of the day, charming shops, and hip cafes. Annapolis is the home of the United States Naval Academy, and tours of the grounds and buildings are always a popular activity. Stroll through the beautiful grounds or take a self-guided tour through the Naval History Museum.

Check out the Banneker-Douglass Museum, which tells the stories of Benjamin Banneker and Frederick Douglass, two black men and leaders who fought against slavery. The museum is free, full of history, and housed in the historic Mount Moriah African Methodist Episcopal Church. Other top sites in the city include Ego Alley, where you can stroll along the water’s edge on Dock Street, William Paca House and Garden, and the Maryland State House.

Part of Annapolis’s charm is the local culture. People in this town tend to be polite, friendly, and very relaxed.

Best Time to Visit Annapolis

The best time to visit Annapolis is in the spring. Boats and rowers line the waterways and the flowers are in full bloom, making the small city even more beautiful.

Price and Availability in Annapolis

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The cheapest day to stay at a vacation rental in Annapolis tends to be Tuesday, while the most expensive day tends to be Friday. Vacation homes in Annapolis tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Annapolis is in May, while the cheapest month is in December. The most popular time to book a vacation rental in Annapolis is in the high season in September. Annapolis has its low season in January, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Annapolis

Rainy days
62° 22°
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82° 26°
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76° 36°
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84° 37°
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90° 57°
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96° 70°
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92° 66°
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88° 50°
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78° 45°
6
73° 31°
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63° 24°
5
71° 23°
2
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Rainy days

This climate histogram shows you the weather patterns in Annapolis. The hottest month in Annapolis is June, when temperatures peak at 96 ˚F. The coolest month is November, when temperatures drop to 22 ˚F. The wettest month in Annapolis is May with 8.99 inches of rain, while the driest month is November with 1.72 inches of rain.

What Expert Travelers Think

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Vacation Rentals in Annapolis

Browse rentals from all the best providers including Airbnb, Priceline, Agoda and many more at AllTheRooms.com. Annapolis has 1,376 hotels, vacation rentals and other special places to stay, with prices to suit budget travelers, luxury travelers and everything in between. When traveling on a budget, the cheapest place to stay in Annapolis is available at $24 per night. The average price of a rental is generally $360 per night.

If you need internet access during your stay in Annapolis, then you can choose from over 669 places to stay that have WiFi internet. 97 of our accommodations come with breakfast in the price. Choose from 47 places to stay that provide gym facilities, so you don't miss a single workout. Driving to Annapolis? Then choose one of the 636 places to stay that comes with a parking spot included. We track 59 accommodations that have a pool or jacuzzi.

Those traveling with a dog, cat or some other animal can stay in any of 142 accommodations that are designated as pet-friendly.

We combine a wide variety of Annapolis accommodations including vacation rentals, home stays, hostels and other unique places to stay into one easy search. We show results from more than 3 providers, including 685 places to stay from Airbnb, 11 accommodations from Priceline and 7 places to stay from Agoda.

838 of the accommodations in Annapolis have been reviewed and rated. 62% are rated great. 483 accommodations allow instant booking.

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