Annapolis Vacation Rentals

Check prices for these upcoming dates

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 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
78° 45°
6
73° 31°
5
63° 24°
5
71° 23°
2
62° 22°
2
82° 26°
2
76° 36°
6
84° 37°
2
90° 57°
4
96° 70°
3
92° 66°
9
88° 50°
7
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Rainy days

This climate histogram shows you the weather patterns in Annapolis. The warmest months in Annapolis are June and May, when temperatures reach 96 ˚F. The coolest month is November, when temperatures drop to 22 ˚F. The wettest month in Annapolis is May with 8.99 inches of rain, while the driest month is November with 1.72 inches of rain.

What Expert Travelers Think

  • — I love AllTheRooms because it is not only local homes for renting, and not only hotels, but everything combined. When I am about to book a place to stay, I usually spend a couple of hours looking through both hotel sites and local home sites, comparing the prices and places.

    Alli Sims
    Alli SimsAlli Sims
  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad
  • — My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!

    Daniella Flores
    Daniella FloresILIKETODABBLE

Vacation Rentals in Annapolis

At AllTheRooms.com we have rentals from all of your favorite providers - Airbnb, Priceline, Agoda and others. AllTheRooms has 1,376 rentals, hotels and other great places to stay during your time in Annapolis, with everything from cheap hostels and homestays to luxury Airbnbs and hotels. For those traveling on a budget, the cheapest place to stay in Annapolis is available at $24 per night. In general, a place to stay in Annapolis will cost you $360 per night.

If you want internet access during your stay in Annapolis, then you can choose from over 669 places to stay that provide WiFi internet. We have 97 accommodations that include a breakfast included. You can keep up with your workout routine by staying at one of 47 accommodations that provide gym facilities. If you are driving to Annapolis, you'll want to pick from 636 places to stay that provide parking. We have 59 vacation rentals that have a pool or jacuzzi.

If you're traveling with a furry friend, then make sure to choose one of the 142 pet-friendly accommodations available.

We combine a wide variety of Annapolis accommodations including vacation rentals, home stays, hostels and other unique places to stay into one easy search. We show results from more than 3 providers, including 685 places to stay from Airbnb, 11 accommodations from Priceline and 7 places to stay from Agoda.

838 of the places to stay in Annapolis have been reviewed by previous guests. They rated 62% as great. 483 accommodations allow instant booking.

Destinations near Annapolis

  • Ocean City6,728 Properties
  • Oakland2,350 Properties
  • McHenry1,828 Properties
  • Swanton1,432 Properties
  • Baltimore1,150 Properties
  • Bethesda622 Properties
  • Ocean Pines494 Properties
  • Silver Spring481 Properties
  • Frederick421 Properties
  • Cambridge389 Properties
  • Rockville353 Properties
  • Berlin343 Properties
  • Gaithersburg318 Properties
  • Oxon Hill304 Properties
  • Laurel299 Properties
  • Columbia295 Properties
  • Salisbury261 Properties
  • Hanover238 Properties
  • Fort Washington204 Properties
  • Aberdeen202 Properties
  • Takoma Park196 Properties
  • Easton195 Properties
  • Stevensville174 Properties
  • Hyattsville165 Properties
  • Chestertown158 Properties
  • St. Michaels100 Properties
  • College Park92 Properties
  • North Beach57 Properties
  • Mount Rainier53 Properties
  • Accokeek48 Properties
  • Chesapeake Beach43 Properties
  • Lusby41 Properties
  • West Ocean City21 Properties
  • Emmitsburg11 Properties