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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Apartment in Annapolis
New Downtown Annapolis Condo With Free Parking
2 bedrooms, 2 beds, 2 private bathrooms
15–20 Nov
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4.98 out of 5 average rating, 165 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
16–21 Aug
4.93 out of 5 average rating, 190 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed
29 Aug – 3 Sept
4.95 out of 5 average rating, 186 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, 187 reviews
Room in Bowie
Cozy Private Queen Room | Free Parking | Near DC
1 queen bed
22–27 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds
21–26 Aug
4.92 out of 5 average rating, 1132 reviews
Hotel room in Annapolis
Historic Inn Stay | Steps from Maryland State
1 bedroom, 1 double bed
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
1 queen bed
17–22 Aug
4.96 out of 5 average rating, 423 reviews
Top guest favourite
Room in Stevensville
Rustic & Elegant Private Bed & Bath
1 bed
30 Aug – 4 Sept
4.98 out of 5 average rating, 305 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, 180 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds
17–22 Aug
4.93 out of 5 average rating, 60 reviews
Guest favourite
Rooms in Arnold
Annapolis Room - 3 miles from Naval Academy
2 bedrooms, 3 beds
15–20 Aug
4.86 out of 5 average rating, 103 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, 276 reviews
Guest favourite
Rooms in Edgewater
Cheerful 2 bedroom shared home with water views
2 bedrooms, 2 queen beds
16–21 Aug
4.86 out of 5 average rating, 92 reviews
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed
17–22 Oct
5.0 out of 5 average rating, 222 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed
15–20 Aug
4.96 out of 5 average rating, 225 reviews
Guest favourite
Flat in Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
1 bedroom, 3 beds
16–21 Aug
4.92 out of 5 average rating, 520 reviews
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds
23–28 Aug
4.96 out of 5 average rating, 168 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
1–6 Sept
4.98 out of 5 average rating, 163 reviews