Annapolis Vacation Rentals - HolidayHomes base64Hash Annapolis Vacation Rentals - HolidayHomes

Annapolis Vacation Rentals

Browse 999 available vacation homes and compared across 7 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

We use AI to generate the short summary in each offer below, check full description before booking.
House Annapolis

Beautiful Waterfront Townhome In Historic Annapolis

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House Annapolis

House with barbeque

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House Annapolis

Fully equipped house with barbeque & patio

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House Annapolis

Pet Friendly-newly built house in peaceful beach community, located in Riva MD.

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House Annapolis

Charming brick home with patio, WiFi, AC, & W/D - walk to everything

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House Annapolis

Heart of Historic District!

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House Annapolis

Waterfront Retreat in Riva· Pool, Pier & Kayaks · Sleeps 9 · 15 Min to Annapolis

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Houseboat Annapolis

Lovely boat with patio

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Apartment Annapolis

Waterfront Oasis of Annapolis Star

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House Annapolis

House with jacuzzi, patio & yard | Nature view

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Apartment Annapolis

Children-friendly lovely apartment with BBQ, garden & patio | Nature view | Close to the beach

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House Annapolis

House with yard, grill & terrace | Perfect for remote work

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House Annapolis

Family-friendly house with grill, private pool & hot tub | Perfect for remote work | Dogs allowed

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House Annapolis

Vacation home with patio & garden | Nature view | Perfect for remote work

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House Annapolis

Vacation home with barbeque & patio

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Top 15 most Recommended Vacation Rentals in Annapolis

Discover your ideal Annapolis vacation rental with real-time comparisons of 999 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

We use AI to generate the short summary in each offer below, check full description before booking.
House Annapolis
House ∙ 18 guests ∙ 6 bedrooms

Vacation home with jacuzzi, BBQ & garden | Good for workation

Annapolis, Anne Arundel County, Maryland, United States
This spacious house rental in Annapolis accommodates 18 guests and features a private pool for a relaxing getaway.
from $839
per night
(11)
View deal
House Annapolis
House ∙ 10 guests ∙ 5 bedrooms

House with yard, grill & hot tub

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis accommodates 11 guests and features a spacious yard perfect for family gatherings.
from $1,364
per night
(25)
View deal
House Annapolis
House ∙ 4 guests ∙ 2 bedrooms

Family-oriented pleasant house with garden & patio

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis Neck accommodates 4 guests and features a cozy fireplace for a warm, inviting atmosphere.
from $238
per night
(11)
View deal
House Annapolis
House ∙ 7 guests ∙ 3 bedrooms

Family-oriented spacious vacation home with terrace, garden & hot tub | City view | Pets are welcome

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Edgewater accommodates 7 guests and features a family-friendly kitchen for enjoyable meals together.
from $432
per night
(110)
View deal
House Annapolis
House ∙ 8 guests ∙ 4 bedrooms

House with patio, grill & yard | City view

Annapolis, Anne Arundel County, Maryland, United States
This house rental in Annapolis accommodates 8 guests and features a spacious yard for outdoor activities.
from $445
per night
(32)
View deal
Condo Annapolis
Condo ∙ 6 guests ∙ 2 bedrooms

Fully equipped condo with barbeque, terrace & pool | Dogs allowed

Annapolis, Anne Arundel County, Maryland, United States
This spacious condo in Annapolis accommodates 6 and features a beautiful waterfront view with access to a pool.
from $185
per night
(24)
View deal
House Annapolis
House ∙ 8 guests ∙ 4 bedrooms

Family-friendly nice house with garden & BBQ | Good for workation

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 $439
per night
(4)
View deal
House Annapolis
House ∙ 8 guests ∙ 4 bedrooms

Family-friendly vacation home with yard, barbeque & hot tub | Nature view

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 $581
per night
(1)
View deal
House Annapolis
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with patio, BBQ & garden

Annapolis, Anne Arundel County, Maryland, United States
Spacious house rental near Naval Academy accommodates 8 guests and features a cozy fireplace for a warm atmosphere.
from $1,945
per night
(7)
View deal

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