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Search results; Over 1,000 homes in Annapolis

Guest favourite
Apartment in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 bed, 1 bath
Aug 23–28
,
4.89 out of 5 average rating, 368 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 baths
Aug 16–21
4.93 out of 5 average rating, 189 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 baths
Sep 20–25
4.95 out of 5 average rating, 186 reviews
Top guest favourite
Room in Annapolis
“Room at the Inn…”
1 queen bed, 1 bath
Aug 16–21
5.0 out of 5 average rating, 33 reviews
Guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed, 1 bath
Aug 16–21
4.96 out of 5 average rating, 134 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed, 1 bath
Aug 29–Sep 3
4.98 out of 5 average rating, 163 reviews
Top guest favourite
Room in Stevensville
Rustic & Elegant Private Bed & Bath
1 bed, 1 bath
Aug 23–28
4.98 out of 5 average rating, 304 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 bath
Nov 1–6
4.92 out of 5 average rating, 1132 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 baths
Sep 6–11
4.94 out of 5 average rating, 187 reviews
Home in Pasadena
Cozy Riviera Beach Retreat Near BWI & Annapolis
3 bedrooms, 3 beds, 1.5 baths
Aug 17–22
New place to stay
Top guest favourite
Apartment in Annapolis
Serene Hideaway
1 bedroom, 2 beds, 1 bath
Aug 30–Sep 4
5.0 out of 5 average rating, 32 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds, Half-bath
Aug 17–22
4.93 out of 5 average rating, 60 reviews
Top guest favourite
Apartment in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 baths
Aug 23–28
4.93 out of 5 average rating, 85 reviews
Room in Bowie
Cozy Private Queen Room | Free Parking | Near DC
1 queen bed, 1 bath
Aug 17–22
5.0 out of 5 average rating, 3 reviews
Hotel in Annapolis
Close to U.S. Naval Academy + Breakfast. Pool. Gym
1 bedroom, 1 king bed, 1 bath
Aug 12–17
4.59 out of 5 average rating, 22 reviews
Hotel room in Annapolis
Historic Inn Stay | Steps from Maryland State
1 bedroom, 1 double bed, 1 bath
Aug 16–21
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
2 bedrooms, 4 beds, 2 baths
Aug 17–22
4.97 out of 5 average rating, 258 reviews
Top guest favourite
Guest suite in Arnold
Coastal Comfort Retreat near Annapolis, EV charger
1 bedroom, 2 beds, 1 bath
Aug 12–17
4.94 out of 5 average rating, 219 reviews
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds, 1 bath
Nov 29–Dec 4
4.97 out of 5 average rating, 457 reviews