Annapolis Vacation Rentals

Compare 867 available properties from 18 providers
Annapolis
Save up to 31%

Best Vacation Home Deals in Annapolis

-31%
Apartment ∙ 4 guests ∙ 2 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $273 $398
VRBO
5.0
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-23%
House ∙ 6 guests ∙ 2 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $361 $472
VRBO
5.0
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-19%
House ∙ 5 guests ∙ 2 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $309 $383
VRBO
5.0
View deal

Discover a vacation home matching your expectations among the 871 great options from more than 18 providers in Annapolis. By comparing these properties, HomeToGo features the best deals as well as the highest rated properties in Annapolis.

Recommended Vacation Rentals in Annapolis

Find your perfect vacation rental in Annapolis: from $33 per night

Private room ∙ 2 guests
Hillsmere Shores, Anne Arundel County, Maryland, United States
from $54
Homestay.com
5.0
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Apartment ∙ 5 guests ∙ 2 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $133
VRBO
5.0
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House ∙ 7 guests ∙ 3 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $398
VRBO
4.9
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Apartment ∙ 5 guests ∙ 2 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $215
VRBO
4.9
View deal
House ∙ 4 guests ∙ 1 bedroom
Annapolis, Anne Arundel County, Maryland, United States
from $121
VRBO
4.7
View deal
Apartment ∙ 6 guests ∙ 1 bedroom
Annapolis, Anne Arundel County, Maryland, United States
from $183
VRBO
4.9
View deal
Apartment ∙ 4 guests ∙ 1 bedroom
Annapolis, Anne Arundel County, Maryland, United States
from $136
VRBO
4.7
View deal
Apartment ∙ 4 guests ∙ 1 bedroom
Annapolis, Anne Arundel County, Maryland, United States
from $165
VRBO
4.6
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House ∙ 4 guests ∙ 2 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $268
VRBO
4.9
View deal
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Vacation Rentals With Fireplaces

Fireplace
Apartment ∙ 4 guests ∙ 2 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $273
VRBO
5.0
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Fireplace
House ∙ 6 guests ∙ 2 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $125
Airbnb
5.0
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Fireplace
House ∙ 6 guests ∙ 3 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $220
Airbnb
4.0
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Dog-Friendly Vacation Rentals

Pet-friendly
Apartment ∙ 6 guests ∙ 3 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $191
VRBO
4.7
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Pet-friendly
House ∙ 6 guests ∙ 3 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $203
Airbnb
5.0
View deal
Pet-friendly
House ∙ 7 guests ∙ 3 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $495
Airbnb
5.0
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Vacation Homes With Fishing Spots Nearby

Fishing
House ∙ 9 guests ∙ 3 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $338
VRBO
5.0
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Fishing
House ∙ 8 guests ∙ 3 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $487
VRBO
4.6
View deal
Fishing
House ∙ 10 guests ∙ 4 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from $609
VRBO
4.7
View deal
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Popular Rental Amenities in Annapolis

  • Internet (821)
  • AC (811)
  • Kitchen (789)
  • TV (761)
  • Washer (663)
  • Microwave (423)
  • Fireplace (345)
  • Dishwasher (332)
  • Grill (278)
  • Yard (254)
  • No smoking (230)
  • Parking (205)
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."

Price and Availability Index in Annapolis

Vacation Rental Price Information in Annapolis

The price graph will give you the nightly price average for the upcoming months of the year. Annapolis is more expensive in October (10/19 - 10/26), where prices are on average $431 a night. The week with the lowest average prices is in May (5/18 - 5/25).

Rental Availability Information in Annapolis

This graph shows the vacation rental availability rate for the next twelve months. Be careful if you plan to go to Annapolis in May, as it comprises the busiest week of the next 12 months (5/18 - 5/25). May (5/11 - 5/18) has got the highest percentage of available rentals.

The Weather in Annapolis

43°
30°
45°
32°
54°
37°
64°
48°
73°
59°
82°
68°
86°
73°
84°
72°
79°
66°
68°
54°
55°
41°
50°
37°
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 86°. However, temperatures can go lower than 30° in Annapolis in January. The rainiest month is July while the driest month is September.

Accommodations in Annapolis

597 among the 871 listed properties in Annapolis are house rentals. They account for many of the accommodation types in this destination (62.78%). Additionally, the standard size of house rentals in Annapolis is 2,390 ft² with an average price of $428 a night. Moreover, most house rentals in this destination can host 7 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 $201 per night on average and have an average size of 990 ft².

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 871 properties
Art & Culture

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.

Nightlife

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.

Local Attractions

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 300 providers, including:

Booking.com Vacation Rentals in Annapolis VRBO Vacation Rentals in Annapolis HomeAway Vacation Rentals in Annapolis TripAdvisor Vacation Rentals in Annapolis VacationRentals.com Vacation Rentals in Annapolis HouseTrip Vacation Rentals in Annapolis FlipKey Vacation Rentals in Annapolis 9flats.com Vacation Rentals in Annapolis VaycayHero Vacation Rentals in Annapolis PerfectPlaces.com Vacation Rentals in Annapolis Homestay.com Vacation Rentals in Annapolis Only-apartments Vacation Rentals in Annapolis Interhome Vacation Rentals in Annapolis Bedycasa Vacation Rentals in Annapolis Novasol Vacation Rentals in Annapolis HomeEscape Vacation Rentals in Annapolis

Vacation Destinations Near Annapolis