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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Guest house in Annapolis
Comfortable Cottage Near Downtown Annapolis
1 bedroom, 1 bed, 1 private bathroom
26–31 Aug
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4.97 out of 5 average rating, 266 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
23–28 Aug
4.93 out of 5 average rating, 191 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed
20–25 Sept
4.95 out of 5 average rating, 187 reviews
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
1 queen bed
24–29 Aug
4.96 out of 5 average rating, 426 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 king bed
20–25 Sept
4.9 out of 5 average rating, 362 reviews
Top guest favourite
Room in Annapolis
A Cottage Room in Presidents Hill
1 single bed
12–17 Sept
4.88 out of 5 average rating, 181 reviews
Top guest favourite
Home in Shady Side
Canary Pointe-A popular getaway for 2!
1 bedroom, 2 beds
20–25 Sept
4.98 out of 5 average rating, 279 reviews
Guest favourite
Rooms in Edgewater
Cheerful 2 bedroom shared home with water views
2 bedrooms, 2 queen beds
21–26 Aug
4.86 out of 5 average rating, 93 reviews
Top guest favourite
Guest suite in Arnold
Coastal Comfort Retreat near Annapolis, EV charger
1 bedroom, 2 beds
23–28 Aug
4.94 out of 5 average rating, 222 reviews
Top guest favourite
Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
2 bedrooms, 4 beds
20–25 Aug
4.97 out of 5 average rating, 258 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 2 beds
24–29 Aug
4.93 out of 5 average rating, 86 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds
20–25 Sept
4.97 out of 5 average rating, 97 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds
28 Aug – 2 Sept
4.92 out of 5 average rating, 61 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
13–18 Sept
4.94 out of 5 average rating, 189 reviews
Top guest favourite
Room in Severna Park
Severna Park Private Entry Suite
2 beds
20–25 Aug
4.98 out of 5 average rating, 64 reviews
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds
29 Nov – 4 Dec
4.97 out of 5 average rating, 459 reviews
Guest favourite
Rooms in Arnold
Annapolis Room - 3 miles from Naval Academy
2 bedrooms, 3 beds
20–25 Aug
4.86 out of 5 average rating, 103 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
23–28 Aug
4.89 out of 5 average rating, 369 reviews
Hotel room in Annapolis
Governor Calvert King | Historic Inns
1 bedroom, 1 king bed
23–28 Aug
4.62 out of 5 average rating, 37 reviews