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Annapolis Vacation Rentals

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 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 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 Weather in Annapolis

95º 59º
3.37
96º 65º
8.8
94º 61º
7.64
95º 62º
4.93
88º 40º
3.81
78º 27º
7.33
63º 28º
5.35
61º
1.36
83º 19º
5.7
78º 31º
2.42
86º 37º
3.28
90º 50º
7.45
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This climate histogram shows you the weather patterns in Annapolis. The warmest months in Annapolis are June and July, when temperatures reach 96 ˚F. The coolest month is January, when temperatures drop to 6 ˚F. The wettest month in Annapolis is July with 8.8 inches of rain, while the driest month is January with 1.36 inches of rain.

What Expert Travelers Think

Vacation Rentals in Annapolis

Choose the perfect accommodation for your vacation at AllTheRooms.com. We aggregate Airbnb, Priceline, Bed and Breakfast and many more. We have 1,110 vacation rentals, hotels and other accommodation types in Annapolis ranging from budget options to luxury places to stay. A trip to Annapolis can be budget-friendly - our cheapest price rental is available at $25 a night. On average, an accommodation in Annapolis will cost you $375 per night.

Those looking to get some work done during their trip to Annapolis can choose from 679 places to stay that have WiFi. 87 of our accommodations come with breakfast in the price. Fitness addicts can get a workout in during their stay by choosing from 47 accommodations that have gym facilities. Driving to Annapolis? Then choose one of the 628 places to stay that comes with a parking spot included. We have 45 accommodations that have a pool or jacuzzi.

Those traveling with a dog, cat or some other animal can stay in any of 185 accommodations that are designated as pet-friendly.

We aggregate vacation rentals, hotels and other bespoke accommodation types from many providers in Annapolis, including 538 places to stay from Airbnb, 7 accommodations from Priceline and 7 places to stay from Bed and Breakfast

676 of our rentals in Annapolis have been reviewed by previous guests. They rated 57% as great. 292 places to stay in are instantly bookable.