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
90° 44°
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93° 56°
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92° 62°
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91° 63°
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87° 55°
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80° 48°
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74° 31°
1
69° 29°
1
56° 24°
2
57° 24°
4
83° 27°
4
87° 33°
2
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Rainy days

This climate histogram shows you the weather patterns in Annapolis. The warmest months in Annapolis are July and June, when temperatures reach 93 ˚F. The coolest month is November, when temperatures drop to 24 ˚F. The wettest month in Annapolis is May with 7.34 inches of rain, while the driest month is January with 0.64 inches of rain.

What Expert Travelers Think

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Vacation Rentals in Annapolis

Browse places to stay from all the leading providers including Airbnb, Priceline, Agoda and more at AllTheRooms.com. We have 1,376 vacation rentals, hotels and other places to stay in Annapolis ranging from low-cost options to luxury places to stay. A vacation in Annapolis can be affordable - our cheapest price vacation rental is available at $24 a night. The average price of a rental is $360 per night.

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

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

AllTheRooms compares vacation rentals, hotels and other bespoke accommodation types from loads of providers in Annapolis, including 685 places to stay from Airbnb, 11 accommodations from Priceline and 7 places to stay from Agoda

838 of our accommodations in Annapolis have been rated by previous guests. They rated 62% as excellent or good. 483 places to stay in are instantly bookable.

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