Annapolis Vacation Rentals

Compare 359 available properties from 11 providers
Annapolis
Anytime
2 guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Apartment
Bed & Breakfast
Distance to center
Max. 1 km
Max. 2 km
Max. 5 km
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

Recommended Vacation Rentals in Annapolis

Find your perfect vacation rental in Annapolis: from $96 per night

Apartment Annapolis 2
Apartment ∙ 2 guests ∙ 1 bedroom
Annapolis, Anne Arundel County, Maryland, United States
from $155
Vrbo
5.0/5.0
"Excellent"
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House Annapolis 6
House ∙ 6 guests ∙ 3 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $377
Vrbo
4.9/5.0
"Excellent"
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House Annapolis 4
House ∙ 4 guests ∙ 2 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $277
Vrbo
5.0/5.0
"Excellent"
View deal
House Annapolis 4
-23%
Aug. 21 - Aug. 28
House ∙ 4 guests ∙ 2 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $334 $432
Vrbo
5.0/5.0
"Excellent"
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Apartment Annapolis 4
Apartment ∙ 4 guests ∙ 2 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $256
Vrbo
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Apartment Annapolis 4
Apartment ∙ 4 guests ∙ 2 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $219
Vrbo
5.0/5.0
"Excellent"
View deal
Apartment Annapolis 2
Apartment ∙ 2 guests ∙ 1 bedroom
Annapolis, Anne Arundel County, Maryland, United States
from $96
Vrbo
View deal
House Annapolis 2
House ∙ 2 guests ∙ 2 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $918
Vrbo
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House Annapolis 2
House ∙ 2 guests ∙ 1 bedroom
Annapolis, Anne Arundel County, Maryland, United States
from $302
Vrbo
5.0/5.0
"Excellent"
View deal
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Vacation rentals with a fireplace

House Fireplace Annapolis
Fireplace
House ∙ 5 guests ∙ 2 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $425
Vrbo
5.0/5.0
"Excellent"
View deal
House Fireplace Annapolis
Fireplace
House ∙ 9 guests ∙ 5 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $1,240
Vrbo
5.0/5.0
"Excellent"
View deal
House Fireplace Annapolis
Fireplace
House ∙ 6 guests ∙ 3 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $752
Vrbo
5.0/5.0
"Excellent"
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Apartments with a balcony or patio

House Balcony/Patio Annapolis
Balcony/Patio
House ∙ 8 guests ∙ 3 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $496
Vrbo
4.8/5.0
"Excellent"
View deal
House Balcony/Patio Annapolis
Balcony/Patio
House ∙ 4 guests ∙ 2 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $487
Vrbo
5.0/5.0
"Excellent"
View deal
House Balcony/Patio Annapolis
Balcony/Patio
House ∙ 6 guests ∙ 2 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $385
Vrbo
5.0/5.0
"Excellent"
View deal
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Vacation rentals and apartments with air conditioning

Apartment Aircondition Annapolis
Aircondition
Apartment ∙ 4 guests ∙ 1 bedroom
Annapolis, Anne Arundel County, Maryland, United States
from $407
Vrbo
4.8/5.0
"Excellent"
View deal
Apartment Aircondition Annapolis
Aircondition
Apartment ∙ 2 guests ∙ 1 bedroom
Annapolis, Anne Arundel County, Maryland, United States
from $230
Vrbo
4.7/5.0
"Outstanding"
View deal
Apartment Aircondition Annapolis
-35%
Aug. 21 - Aug. 28
Aircondition
Apartment ∙ 4 guests ∙ 1 bedroom
Annapolis, Anne Arundel County, Maryland, United States
from $265 $406
Vrbo
4.7/5.0
"Outstanding"
View deal
See all offers

Popular Rental Amenities in Annapolis

  • Kitchen (225)
  • Air conditioning (171)
  • TV (166)
  • Microwave (165)
  • Internet (157)
  • No smoking (151)
  • Dishwasher (149)
  • Parking (128)
  • No pets (113)
  • Washer (95)
  • Grill (84)
  • Yard (59)

Filters are provided so you can tailor your search and find a great property in Annapolis. In Annapolis, 285 properties include "TVs". Consequently, if you never miss an episode of your favorite show, use the TVs filter to compare these properties. Plan your vacation in advance if you want a rental with a jacuzzi or you want a rental with a sauna. There are just 4 listed properties with "Jacuzzis" and 5 accommodations with "saunas."

The Weather in Annapolis


-1°

12°
18°
23°
15°
28°
20°
30°
23°
29°
22°
26°
19°
20°
12°
13°
10°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Check out our climate diagram to find the perfect month for your vacation. In July maximum temperatures go higher than 30°. However, temperatures can go lower than -1° in Annapolis in January. The rainiest month is January while the driest month is September.

Accommodations for your vacation in Annapolis

174 among the 359 listed properties in Annapolis are house rentals. They account for many of the accommodation types in this destination (61.48%). Additionally, the standard size of house rentals in Annapolis is 230 m² with an average price of $966 a night. Moreover, most house rentals in this destination can host 9 guests, which makes it a wonderful vacation spot for large groups. If you are interested in a different accommodation type, you may want to have a look at apartment rentals, which are the second most typical accommodation option in Annapolis. These accommodations cost $237 per night on average and have an average size of 99 m².

Dive into the past with an Annapolis vacation rental

Whether they’re colonial cottages or modern condos, vacation rentals in Annapolis are close to the action of this historic yet bustling modern city. With all the comforts of home combined with exciting things to see and do, this scenic area of Maryland will have you returning again and again.

Show all 359 properties
What are the best places to discover the arts and culture of Annapolis?

Art, history, and culture

From its earliest days, Annapolis has been known as the “Athens of America” for its cultural, social and intellectual activities. Your vacation rental in Annapolis will be close to many artistic and cultural offerings, such as Historic London Town and Gardens, where you can explore 23 acres of history, archeology, and beautiful flora.

Experience performances by the Annapolis Shakespeare Company, Ballet Theatre of Maryland, or the Annapolis Symphony Orchestra. If visual art is your cup of tea, there are 25 fine art galleries downtown alone, as well as the Elizabeth Myers Mitchell Gallery, a museum that is open daily and has free admission.

What are the best nightlife spots in Annapolis?

Music and other nightlife

Much of historic Annapolis is walkable. Across the street from the visitors center, in the Arts District, is Rams Head On Stage, a delightful bar/restaurant/concert venue with a healthy offering of music or comedy almost every night. There’s an active music scene in Annapolis, with dozens of local bands calling the area home. See them perform in pubs, bars, and restaurants all over the city, such as Armadillo's Bar and Grill and Castlebay Irish Pub.

Where are the unique attractions in Annapolis?

Sailing and other excursions

Annapolis is known for its sailing and other water activities on the Chesapeake Bay, and there’s always something to see near the harbor, such as the US Naval Academy Museum. There are many tours in the area, on water and on land, including Colonial Tours of Annapolis, Pirate Adventures on the Chesapeake (great for kids), and Segs in the City.

We compare more than 2,000 providers, including:

Booking.com Vacation Rentals in Annapolis TripAdvisor Vacation Rentals in Annapolis Vrbo Vacation Rentals in Annapolis Airbnb Vacation Rentals in Annapolis Novasol Vacation Rentals in Annapolis Inter Chalet Vacation Rentals in Annapolis EveryStay Vacation Rentals in Annapolis Interhome Vacation Rentals in Annapolis 9flats.com Vacation Rentals in Annapolis HouseTrip Vacation Rentals in Annapolis Belvilla Vacation Rentals in Annapolis Sykes Cottages Vacation Rentals in Annapolis Homestay.com Vacation Rentals in Annapolis Ski Planet Vacation Rentals in Annapolis Only-apartments Vacation Rentals in Annapolis James Villa Holidays Vacation Rentals in Annapolis

Vacation Destinations Near Annapolis

Vacation Rentals

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