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Annapolis Vacation Rentals

Browse 1,017 available vacation homes and compared across 11 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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House Annapolis
Amazing Waterfront Retreat with Pool, Pier, and Kayaks, Minutes from Annapolis
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House Annapolis
Fully equipped house with barbeque, terrace & pool
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House Annapolis
Fully equipped beautiful vacation home with patio & garden
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Apartment Annapolis
Holiday apartment with terrace & yard | City view
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House Annapolis
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
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Apartment Annapolis
Waterfront Oasis of Annapolis Star
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House Annapolis
Quiet Relaxing Waterfront Suisse Chalet
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House Annapolis
House with jacuzzi, patio & yard | Nature view
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House Annapolis
Sophisticated Charmer with Parking & Views of the USNA Chapel Dome
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House Annapolis
Vacation home with garden & patio
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House Annapolis
Historic Annapolis~~New interior~~5 parking spaces~~6BR, 4BA
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House Annapolis
Vacation home with 3 rooms for 6 persons
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House Annapolis
House with terrace & grill
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House Annapolis
Vacation home with terrace | City view
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Top 15 most Recommended Vacation Rentals in Annapolis

Discover your ideal Annapolis vacation rental with real-time comparisons of 1,017 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Annapolis
16 guests ∙ 5 bedrooms

House

Annapolis, Anne Arundel County, Maryland, United States
Spacious house rental in Annapolis for 16 guests with a hot tub and ample parking available.
from $1,288
per night
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House Annapolis
8 guests ∙ 3 bedrooms

House

Annapolis, Anne Arundel County, Maryland, United States
Spacious house rental near Naval Academy accommodates 8 guests and features a cozy fireplace for a comfortable stay.
from $425
per night
(21)
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House Annapolis
7 guests ∙ 3 bedrooms

House

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis accommodates 7 guests and features a spacious yard for outdoor enjoyment.
from $344
per night
(10)
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House Annapolis
8 guests ∙ 4 bedrooms

House

Annapolis, Anne Arundel County, Maryland, United States
Spacious house rental in Annapolis for 8 guests featuring a cozy fireplace and a large yard perfect for families.
from $455
per night
(98)
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House Annapolis
5 guests ∙ 3 bedrooms

House

Annapolis, Anne Arundel County, Maryland, United States
Charming house rental in Annapolis for 5 guests featuring a spacious yard perfect for family gatherings.
from $356
per night
(13)
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House Annapolis
12 guests ∙ 6 bedrooms

House

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis accommodates 12 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $849
per night
(84)
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House Annapolis
House ∙ 8 guests ∙ 3 bedrooms

195 m² House

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis accommodates 8 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $613
per night
(82)
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House Annapolis
14 guests ∙ 6 bedrooms

House

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis accommodates 14 guests and features a spacious yard for outdoor activities.
from $993
per night
(51)
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House Annapolis
House ∙ 12 guests ∙ 3 bedrooms

204 m² House

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis accommodates 12 guests and features a family-friendly kitchen.
from $753
per night
(50)
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