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
63° 16°
5
74° 22°
2
80° 23°
3
84° 37°
5
89° 47°
3
95° 58°
4
93° 64°
7
95° 63°
4
87° 51°
2
77° 38°
5
78° 25°
2
62°
4
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Rainy days

This climate histogram shows you the weather patterns in Annapolis. The hottest month in Annapolis is May, when temperatures peak at 95 ˚F. The coolest month is January, when temperatures drop to 8 ˚F. The wettest month in Annapolis is June with 7.02 inches of rain, while the driest month is November with 1.96 inches of rain.

What Expert Travelers Think

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Vacation Rentals in Annapolis

Browse vacation rentals from all the leading providers including Airbnb, Priceline, Agoda and many more at AllTheRooms.com. AllTheRooms has 1,376 rentals, hotels and other great places to stay while you enjoy Annapolis, with everything from cheap hostels and homestays to extravagant Airbnbs and hotels. When traveling on a budget, the cheapest place to stay in Annapolis is available at $24 per night. On average, an accommodation in Annapolis will cost you $360 per night.

Those looking to get some work finished during their trip to Annapolis can choose from 669 places to stay that have WiFi. We have 97 accommodations that come with breakfast included. Fitness addicts can get a workout in during their stay by choosing from 47 accommodations that have gyms. If you're planning on getting to Annapolis by car, be sure to choose from 636 accommodations that provide parking. 59 hotels and vacation rentals come with a pool or jacuzzi

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

AllTheRooms compares vacation rentals, hotels and other bespoke accommodation types from many 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 reviewed and rated. 62% are rated great. 483 accommodations allow instant booking.

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