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
Apartment in Annapolis
4.96 out of 5 average rating, 122 reviewsCharming lower-level apartment in Annapolis
10–17 Jul
$252 NZD per night
Guest favourite
Guest suite in Arnold
4.85 out of 5 average rating, 497 reviewsSunny Spot Suite, Serene, Annapolis, Naval Academy
5–12 Jul
$224 NZD per night
Guest favourite
Guest suite in Annapolis
4.97 out of 5 average rating, 162 reviewsPrivate 2B Apt--less than 1 mi to Downtown
11–18 Mar
$312 NZD per night
Guest favourite
Boat in Annapolis
4.94 out of 5 average rating, 351 reviewsStay aboard the S/V MY STUDIO on Annapolis Harbor
28 Mar – 4 Apr
$393 NZD per night
Guest favourite
Guest suite in Arnold
4.96 out of 5 average rating, 563 reviewsOld Bay Bungalow
22–29 May
$353 NZD per night
Guest favourite
Condo in Annapolis
4.96 out of 5 average rating, 53 reviewsFunky Uptown Apt meets Downtown - Hist District
11–18 Jun
$305 NZD per night
Guest favourite
Guest suite in Arnold
4.96 out of 5 average rating, 24 reviewsCozy cottage with riverview and pool
7–14 Mar
$269 NZD per night
Guest favourite
Apartment in Annapolis
4.92 out of 5 average rating, 65 reviewsEastport Bungalow
8–15 Sep
$320 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
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- Rentals with a washing machine and dryer Annapolis
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