Vacation rentals in Annapolis
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Top-rated vacation rentals in Annapolis
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Annapolis vacation rentals
Other great vacation rentals in Annapolis
Guest favourite
Guest suite in Annapolis
4.97 out of 5 average rating, 164 reviewsPrivate 2B Apt--less than 1 mi to Downtown
Jan. 14 – 21
$251 CAD per night
Guest favourite
Apartment in Annapolis
4.96 out of 5 average rating, 123 reviewsCharming lower-level apartment in Annapolis
Sep. 26 – Oct. 3
$205 CAD per night
Guest favourite
Home in Annapolis
4.95 out of 5 average rating, 349 reviewsNew Hotel Chic
Jan. 20 – 27
$302 CAD per night
Guest favourite
Apartment in Edgewater
4.92 out of 5 average rating, 400 reviewsPet Friendly Garden Apartment Near Annapolis
Oct. 20 – 27
$181 CAD per night
Guest favourite
Boat in Annapolis
4.94 out of 5 average rating, 352 reviewsStay aboard the S/V MY STUDIO on Annapolis Harbor
Nov. 30 – Dec. 7
$295 CAD per night
Guest favourite
Guesthouse in Annapolis
5.0 out of 5 average rating, 106 reviewsGarden View, a spacious 1 bedroom with loft.
Nov. 4 – 11
$270 CAD per night
Guest favourite
Condo in Annapolis
4.96 out of 5 average rating, 54 reviewsFunky Uptown Apt meets Downtown - Hist District
Aug. 17 – 24
$237 CAD per night
Guest favourite
Home in Annapolis
4.95 out of 5 average rating, 41 reviewsNaptown Suite
Jun. 5 – 12
$189 CAD per night
Quick stats about vacation rentals in Annapolis
Total rentals
640 properties
Rentals with dedicated workspaces
350 properties have a dedicated workspace
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
180 properties allow pets
Family-friendly rentals
440 properties are a good fit for families
Total number of reviews
28K reviews
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