Holiday houses in Annapolis
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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
Guest favourite
Guest suite in Annapolis
4.97 out of 5 average rating, 164 reviewsPrivate 2B Apt--less than 1 mi to Downtown
3–10 Mar
$305 NZD per night
Guest favourite
Apartment in Annapolis
4.96 out of 5 average rating, 123 reviewsCharming lower-level apartment in Annapolis
21–28 Aug
$249 NZD per night
Guest favourite
Cottage in Annapolis
4.94 out of 5 average rating, 314 reviewsWright’s Cottage, Pets Welcome!
22–29 Jul
$366 NZD per night
Guest favourite
Apartment in Edgewater
4.92 out of 5 average rating, 399 reviewsPet Friendly Garden Apartment Near Annapolis
10–17 Sep
$220 NZD per night
Guest favourite
Home in Annapolis
4.95 out of 5 average rating, 349 reviewsNew Hotel Chic
6–13 Mar
$366 NZD per night
Guest favourite
Cottage in Annapolis
4.96 out of 5 average rating, 338 reviewsRelaxing Water Views - Mill Creek Cottage
11–18 Jan
$394 NZD 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
6–13 Aug
$358 NZD per night
Guest favourite
Condo in Annapolis
4.96 out of 5 average rating, 54 reviewsFunky Uptown Apt meets Downtown - Hist District
17–24 Aug
$289 NZD per night
Quick stats about holiday 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
Destinations to explore
- Baltimore Holiday rentals
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- Apartment rentals Annapolis
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