We use cookies to provide you with the best browsing experience. The data collected by cookies is used to optimise the website for our users and deliver an appropriate service and relevant information to you. By using our site we assume you’re aware and agree to use the cookies for this purpose.

OKLearn more
Destination Photo

Annapolis Vacation Rentals

Search

Our Favorite Vacation Rentals in Annapolis

See all 1,110 deals in Annapolis

Annapolis Vacation Rentals with a Pool

See all deals in Annapolis with a pool

Annapolis Vacation Rentals with Wi-Fi

See all deals in Annapolis with WiFis

Annapolis Pet-Friendly Vacation Rentals

See all deals in Annapolis that allow pets

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

Most expensive
Most availability
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
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

86º 37º
3.28
90º 50º
7.45
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 6º
1.36
83º 19º
5.7
78º 31º
2.42
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Rainy days
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 trip at AllTheRooms.com. We aggregate Airbnb, VRBO, Homeaway and more. Annapolis has 1,104 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 $20 per night. A typical accommodation in Annapolis costs on average $376 per night.

If you need an internet connection during your stay in Annapolis, then you can choose from over 680 places to stay that provide WiFi internet. 88 of our accommodations in include a breakfast in the price. Choose from 48 places to stay that provide gym facilities, so you won't miss a single workout. If you're planning on arriving in Annapolis by car, be sure to choose from 630 accommodations that provide parking. 45 hotels and vacation rentals have a pool or jacuzzi.

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

In Annapolis AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 6 providers, including 537 places to stay from Airbnb, 123 accommodations from VRBO and 123 places to stay from Homeaway.

672 of our accommodations in Annapolis have been reviewed and rated. 57% are rated excellent or good. 293 places to stay in are instantly bookable.

Destinations near Annapolis

  1. Accommodation Search
  2. United States of America
  3. Maryland
  4. Annapolis