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
85° 37°
2
94° 51°
6
98° 58°
2
101° 70°
4
96° 66°
2
96° 57°
0
94° 44°
4
65° 26°
1
60° 22°
2
68° 12°
3
68° 16°
2
80° 24°
3
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 101 ˚F. The coolest month is December, when temperatures drop to 12 ˚F. The wettest month in Annapolis is August with 5.97 inches of rain, while the driest month is April with 0.25 inches of rain.

What Expert Travelers Think

  • — 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
  • — I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips

    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit
  • — Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location

    Jaz
    JazThe Life of a Social Butterfly

Vacation Rentals in Annapolis

Browse accommodations from all the leading providers including Airbnb, Priceline, Agoda and others at AllTheRooms.com. AllTheRooms has 1,376 vacation rentals, hotels and other great places to stay while you enjoy Annapolis, with everything from cheap hostels and homestays to luxury Airbnbs and hotels. A vacation in Annapolis can be budget-friendly - the lowest price rental is available at $24 a night. A typical accommodation in Annapolis costs on average $360 per night.

If you need an internet connection during your stay in Annapolis, then you can choose from over 669 accommodations that provide WiFi internet. 97 of our accommodations come with breakfast in the price. Choose from 47 places to stay that provide gym options, so you don't miss a single workout. Driving to Annapolis? Then choose one of the 636 places to stay that comes with a parking spot included. We track 59 accommodations that have a pool or jacuzzi.

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

We aggregate 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 rentals in Annapolis have been reviewed by previous guests. They rated 62% as excellent or good. 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