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
Home in Annapolis
4.95 out of 5 average rating, 350 reviewsNew Hotel Chic
10 – 17 Mar
$2,320 AUD total
Guest favourite
Guesthouse in Annapolis
4.99 out of 5 average rating, 108 reviewsCoastal Waterfront 1 Bedroom Cottage
16 – 23 July
$4,793 AUD total
Guest favourite
Cottage in Annapolis
4.96 out of 5 average rating, 339 reviewsRelaxing Water Views - Mill Creek Cottage
9 – 16 Jan
$2,488 AUD total
Guest favourite
Apartment in Edgewater
4.92 out of 5 average rating, 400 reviewsPet Friendly Garden Apartment Near Annapolis
3 – 10 July
$1,653 AUD total
Guest favourite
Guest suite in Arnold
4.94 out of 5 average rating, 118 reviewsCoastal Comfort Suite Near Annapolis, Hottub, EV
26 July – 2 Aug
$2,216 AUD total
Guest favourite
Boat in Annapolis
4.94 out of 5 average rating, 352 reviewsStay aboard the S/V MY STUDIO on Annapolis Harbor
8 – 15 July
$2,268 AUD total
Guest favourite
Guest suite in Arnold
4.84 out of 5 average rating, 503 reviewsSunny Spot Suite, Serene, Annapolis, Naval Academy
23 – 30 Oct
$1,401 AUD total
Guest favourite
Condo in Annapolis
4.96 out of 5 average rating, 54 reviewsFunky Uptown Apt meets Downtown - Hist District
12 – 19 Aug
$1,828 AUD total
Quick stats about accommodation 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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