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 Index in Annapolis

Most expensive

Most availability

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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 March. The most popular time to book a vacation rental in Annapolis is in the high season in October. Annapolis has its low season in December, 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

66º 16º

0.58

73º 16º

2.07

70º 24º

0.8

80º 23º

3.23

91º 38º

2.22

93º 45º

4.97

73º 16º

2.07

92º 65º

7.64

93º 64º

5.34

90º 56º

1.71

86º 41º

2.19

73º 16º

2.07

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Rainy days

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This climate histogram shows you the weather patterns in Annapolis. The hottest month in Annapolis is August, when temperatures peak at 93 ˚F. The coolest month is January, when temperatures drop to 16 ˚F. The wettest month in Annapolis is July with 7.64 inches of rain, while the driest month is December with 0.58 inches of rain.

Vacation Rentals in Annapolis

Choose the perfect accommodation for your trip at AllTheRooms.com. We aggregate Airbnb, VRBO, Homeaway and more. Annapolis has 4284 hotels, vacation rentals and other unique places to stay, with prices to suit budget travelers, luxury travelers and everything in between. For those trying to keep costs down, the lowest priced place to stay in Annapolis comes in at $19 per night. On average, a place to stay in Annapolis will cost you $372 per night.

If you need an internet connection during your stay in Annapolis, then you can choose from over 1384 places to stay that provide WiFi internet. 184 places to stay include a breakfast. Choose from 102 places to stay that provide gym facilities, so you won't miss a single workout. If you are driving to Annapolis, you'll want to pick from 1286 places to stay that provide parking. We have 94 places to stay that have a pool or jacuzzi.

Those traveling with a dog, cat or some other animal can stay in one of 372 accommodations that are designated as pet-friendly.

AllTheRooms aggregates vacation rentals, hotels and other unique accommodation types from 6 providers in Annapolis, including 1062 places to stay from Airbnb, 286 accommodations from VRBO and 262 places to stay from Homeaway

2768 accommodations in Annapolis have been reviewed: 58% are rated excellent or good. 1196 accommodations allow instant booking.