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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Miller Cottage - near Navy Stadium
1 bedroom, 2 beds, 1 private bathroom
18–23 Aug
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4.99 out of 5 average rating, 157 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, 187 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, 185 reviews
Top guest favourite
Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
2 bedrooms, 4 beds
17–22 Aug
4.96 out of 5 average rating, 257 reviews
Top guest favourite
Room in Stevensville
Rustic & Elegant Private Bed & Bath
1 bed
23–28 Aug
4.98 out of 5 average rating, 304 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds
9–14 Aug
4.93 out of 5 average rating, 60 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, 361 reviews
Hotel in Annapolis
Close to U.S. Naval Academy + Breakfast. Pool. Gym
1 bedroom, 1 king bed
9–14 Aug
4.55 out of 5 average rating, 20 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, 422 reviews
Guest favourite
Rooms in Edgewater
Cheerful 2 bedroom shared home with water views
2 bedrooms, 2 queen beds
15–20 Aug
4.86 out of 5 average rating, 92 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
6–11 Sept
4.94 out of 5 average rating, 186 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, 457 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed
9–14 Aug
4.96 out of 5 average rating, 224 reviews
Hotel room in Annapolis
Robert Johnson King | Historic Inns | Vintage Vibe
1 bedroom, 1 king bed
23–28 Aug
4.88 out of 5 average rating, 16 reviews
Guest favourite
Flat in Annapolis
Uptown Condo w 2 Parking Spots
1 bedroom
10–15 Aug
5.0 out of 5 average rating, 17 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
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds
18–23 Aug
4.96 out of 5 average rating, 113 reviews
Top guest favourite
Guest house in Annapolis
Guest Suite Getaway near Naval Academy Stadium
1 bed
16–21 Aug
5.0 out of 5 average rating, 173 reviews
Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds
27 Nov – 2 Dec
4.96 out of 5 average rating, 253 reviews