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Search results; Over 1,000 homes in Annapolis

Guest favourite
Flat in Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
1 bedroom, 3 beds, 1 private bathroom
16–21 Aug
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4.92 out of 5 average rating, 520 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
16–21 Aug
4.93 out of 5 average rating, 190 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
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, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
29 Aug – 3 Sept
4.95 out of 5 average rating, 186 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed, 1 bathroom
23–28 Aug
4.89 out of 5 average rating, 368 reviews
Top guest favourite
Room in Annapolis
“Room at the Inn…”
1 queen bed, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 33 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds, WC
17–22 Aug
4.93 out of 5 average rating, 60 reviews
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
1 queen bed, 1 bathroom
24–29 Aug
4.96 out of 5 average rating, 423 reviews
Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 bathroom
27 Nov – 2 Dec
4.96 out of 5 average rating, 253 reviews
Top guest favourite
Room in Annapolis
A Cottage Room in Presidents Hill
1 single bed, 1.5 bathrooms
12–17 Sept
4.88 out of 5 average rating, 180 reviews
Top guest favourite
Room in Stevensville
Rustic & Elegant Private Bed & Bath
1 bed, 1 bathroom
31 Aug – 5 Sept
4.98 out of 5 average rating, 306 reviews
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed, 1 bathroom
17–22 Oct
5.0 out of 5 average rating, 222 reviews
Top guest favourite
Home in Shady Side
Canary Pointe-A popular getaway for 2!
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 276 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
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, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Rooms in Arnold
Annapolis Room - 3 miles from Naval Academy
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.86 out of 5 average rating, 103 reviews
Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds, 1 bathroom
9–14 Sept
4.95 out of 5 average rating, 142 reviews
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 168 reviews