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Holiday rentals in Annapolis
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Annapolis
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Annapolis holiday rentals
Other great holiday rentals in Annapolis
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Guest favourite
Guest suite in Riva
5 out of 5 average rating, 12 reviewsCozy one bedroom appt on the water
![](https://a0.muscache.com/im/pictures/miso/Hosting-727621428905786567/original/1db8f888-b4cc-4fd4-8f4e-c69ac90cc3b1.jpeg?im_w=720)
Guest favourite
Guest suite in Arnold
4.97 out of 5 average rating, 33 reviewsCozy cottage with riverview and pool
![](https://a0.muscache.com/im/pictures/miso/Hosting-613631973348321142/original/a3f9cbee-b19d-48ae-ba3d-178c41a5b207.jpeg?im_w=720)
Guest favourite
Home in Annapolis
4.9 out of 5 average rating, 62 reviewsAdorable 1 bedroom apartment in downtown Annapolis
![](https://a0.muscache.com/im/pictures/624172f2-67fd-46cc-84dc-0b9578c94c3a.jpg?im_w=720)
Guest favourite
Loft in Riva
4.96 out of 5 average rating, 98 reviewsNew Loft w/South River view from treehouse deck!
![](https://a0.muscache.com/im/pictures/airflow/Hosting-697759545857544735/original/4bae274d-06a8-4ca0-992f-be572ca6cd96.jpg?im_w=720)
Guest favourite
Apartment in Annapolis
4.95 out of 5 average rating, 66 reviewsFunky Uptown Apt meets Downtown - Hist District
![](https://a0.muscache.com/im/pictures/8cc3e7f6-9969-433d-94d5-4b9ff7b6f207.jpg?im_w=720)
Guest favourite
Rental unit in Annapolis
4.92 out of 5 average rating, 85 reviewsEastport Bungalow
![](https://a0.muscache.com/im/pictures/9f6ba63f-3e15-4f3d-b61a-722a2d8f228f.jpg?im_w=720)
Guest favourite
Guest house in Edgewater
5 out of 5 average rating, 71 reviews1 large room efficiency in detached garage.
![](https://a0.muscache.com/im/pictures/miso/Hosting-50622405/original/0a14b06f-6acd-4d98-a757-4990cc6013b3.jpeg?im_w=720)
Guest favourite
Home in Crownsville
5 out of 5 average rating, 67 reviews"Hilltop Hideaway"- Private basement suite
Quick stats about holiday rentals in Annapolis
Total rentals
630 properties
Total number of reviews
29K reviews
Family-friendly rentals
430 properties are a good fit for families
Pet-friendly rentals
190 properties allow pets
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
350 properties have a dedicated workspace
Destinations to explore
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