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Search results; Over 1,000 homes in Annapolis

Top guest favorite
Home in Annapolis
Sauna and patio, block from Naval Academy
1 bedroom, 2 beds, 1 private bath
Nov 27 – Dec 2
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4.96 out of 5 average rating, 253 reviews
Top guest favorite
Loft in Annapolis
Exposed brick loft on Main Street
4.92 out of 5 average rating, 1132 reviews, 1 bedroom, 2 beds, 1 bath
Nov 1 – 6
Guest favorite
Room in Annapolis
1926 home, 4 houses from the stadium
4.95 out of 5 average rating, 186 reviews, 1 queen bed, 3 baths
Sep 20 – 25
Guest favorite
Boat in Annapolis
Sleep on the water in Annapolis
4.93 out of 5 average rating, 60 reviews, 1 bedroom, 2 beds, Half-bath
Aug 17 – 22
Guest favorite
Room in Annapolis
1926 Four Square home with fire pit
4.93 out of 5 average rating, 190 reviews, 1 queen bed, 1.5 baths
Aug 16 – 21
Guest favorite
Room in Annapolis
Waterfront suite with a rooftop patio
4.96 out of 5 average rating, 134 reviews, 1 queen bed, 1 bath
Aug 16 – 21
Top guest favorite
Room in Annapolis
Saltwater pool, hot tub, and fire pit
4.94 out of 5 average rating, 358 reviews, 1 king bed, 1 bath
Aug 17 – 22
Top guest favorite
Room in Stevensville
Rustic pine suite near the water
4.98 out of 5 average rating, 304 reviews, 1 bed, 1 bath
Aug 23 – 28
Hotel room in Annapolis
Governor Calvert King | Historic Inns
4.62 out of 5 average rating, 37 reviews, 1 bedroom, 1 bed, 1 bath
Aug 19 – 24
Top guest favorite
Room in Annapolis
2 blocks from the Chesapeake, with gardens
5.0 out of 5 average rating, 33 reviews, 1 queen bed, 1 bath
Aug 16 – 21
Top guest favorite
Guest suite in Arnold
Spa-like shower and a seasonal pool
4.94 out of 5 average rating, 219 reviews, 1 bedroom, 2 beds, 1 bath
Aug 13 – 18
Top guest favorite
Guesthouse in Annapolis
Waterfront on the South River with pool
5.0 out of 5 average rating, 222 reviews, 1 bedroom, 1 bed, 1 bath
Oct 17 – 22
Top guest favorite
Home in Annapolis
Fire pit and patio near Annapolis
4.96 out of 5 average rating, 78 reviews, 2 bedrooms, 3 beds, 2 baths
Aug 15 – 20
Top guest favorite
Apartment in Annapolis
Screened porch one block from Main St
4.93 out of 5 average rating, 85 reviews, 2 bedrooms, 1 bed, 1.5 baths
Aug 23 – 28
Top guest favorite
Apartment in Annapolis
One block from Main Street, open layout
4.91 out of 5 average rating, 114 reviews, 1 bedroom, 1 bed, 1 bath
Aug 30 – Sep 4
Top guest favorite
Cottage in Annapolis
Mill Creek views from a wooded porch
4.97 out of 5 average rating, 469 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 30 – Sep 4
Top guest favorite
Guest suite in Annapolis
Forest suite with pool and hammocks
4.95 out of 5 average rating, 142 reviews, 2 bedrooms, 3 beds, 1 bath
Sep 9 – 15
Top guest favorite
Guest suite in Annapolis
Cathedral ceilings in walkable Murray Hill
4.97 out of 5 average rating, 457 reviews, 1 bedroom, 2 beds, 1 bath
Nov 29 – Dec 4
Top guest favorite
Condo in Annapolis
Renovated Eastport pad with rooftop views
4.96 out of 5 average rating, 168 reviews, 2 beds, 1 bath
Aug 23 – 28