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Annapolis Vacation Rentals

Browse 984 available vacation homes and compared across 13 trusted partners

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Top-Rated Vacation rentals in Annapolis

Book the highest-rated Annapolis vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Annapolis
Fully equipped vacation home with barbeque, terrace & yard | City view
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Condo Annapolis
Family-friendly charming condo with private pool & patio | Nature view
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House Annapolis
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
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House Annapolis
Vacation home with patio & garden
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Apartment Annapolis
Waterfront Oasis of Annapolis Star
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House Annapolis
House with patio, yard & barbeque | City view
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House Annapolis
ACROSS FROM STADIUM - walk to downtown Annapolis.
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House Annapolis
House with jacuzzi, patio & yard | Nature view
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House Annapolis
Vacation home with garden, terrace & grill
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House Annapolis
Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!
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House Annapolis
House with barbeque
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House Annapolis
Lots free parking, hot tub, tree house, outdoor oasis - NOT party house
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House Annapolis
Fully equipped charming house with patio & BBQ | City view | Good for workation
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Apartment Annapolis
Tranquility Awaits
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House Annapolis
Vacation home with barbeque, patio & pool | Good for workation
Book now

Top 15 most Recommended Vacation Rentals in Annapolis

Discover your ideal Annapolis vacation rental with real-time comparisons of 998 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Apartment Annapolis
Apartment ∙ 8 guests ∙ 4 bedrooms

241 m² Apartment

Annapolis, Anne Arundel County, Maryland, United States
This spacious apartment rental in Parole accommodates 8 guests and features a family-friendly environment with convenient parking.
from $246
per night
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House Annapolis
9 guests ∙ 3 bedrooms

House

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis accommodates 9 guests and features a family-friendly kitchen for your convenience.
from $635
per night
(33)
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House Annapolis
8 guests ∙ 4 bedrooms

House

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis accommodates 8 guests and features a family-friendly atmosphere with a fully equipped kitchen.
from $472
per night
(124)
View deal
House Annapolis
9 guests ∙ 3 bedrooms

House

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis accommodates 9 guests and features a spacious kitchen for your convenience.
from $466
per night
(45)
View deal
House Annapolis
House ∙ 8 guests ∙ 4 bedrooms

204 m² House

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis accommodates 8 guests and features a family-friendly kitchen and a spacious yard.
from $407
per night
(49)
View deal
House Annapolis
12 guests ∙ 5 bedrooms

House

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Arundel on the Bay accommodates 12 guests and features a waterfront view and a spacious yard.
from $487
per night
(55)
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House Annapolis
9 guests ∙ 4 bedrooms

House

Annapolis, Anne Arundel County, Maryland, United States
Spacious house rental in Annapolis for 9 with a cozy fireplace and a large yard for outdoor activities.
from $397
per night
(30)
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House Annapolis
7 guests ∙ 4 bedrooms

House

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis accommodates 7 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $399
per night
(112)
View deal
House Annapolis
House ∙ 10 guests ∙ 4 bedrooms

260 m² House

Annapolis, Anne Arundel County, Maryland, United States
Spacious house rental in Annapolis for 10 guests featuring a family-friendly kitchen and a large yard for outdoor activities.
from $617
per night
(185)
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