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
96° 70°
3
92° 66°
9
88° 50°
7
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
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
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

  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School
  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen
  • — When I first opened up the AllTheRooms.com site, I was impressed right away... When I’m traveling, I don’t like to waste time searching multiple engines for accommodations, it gets overwhelming and frustrating fast. I want a unique, comfortable stay for the best deal

    Kaelin
    KaelinKindly Kae

Vacation Rentals in Annapolis

Find the perfect rental for your trip at AllTheRooms.com. We compare Airbnb, Priceline, Agoda and others. AllTheRooms has 1,376 vacation 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 most economical place to stay in Annapolis is available at $24 per night. The average price of a rental is $360 per night.

If you want to stay connected during your trip, then you can choose from over 669 accommodations in Annapolis that have WiFi. 97 places to stay include a morning meal. Fitness fanatics 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 636 places to stay that comes with a parking spot included. We track 59 vacation rentals that have a pool or jacuzzi.

AllTheRooms has 142 pet-friendly places to stay in Annapolis, so if you're traveling with your pet you won't have any trouble.

In Annapolis AllTheRooms currently compares hotels, vacation rentals, hostels from more than 3 providers, including 685 places to stay from Airbnb, 7 accommodations from Priceline and 7 places to stay from Agoda.

838 of our accommodations in Annapolis have been rated by previous guests. They rated 62% as great. You can instantly book any of 483 places to stay right now.

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