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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Guest house in Annapolis
Private Art-Filled Guesthouse near Naval Academy
Studio, 1 bed, 1 private bathroom
16–21 Aug
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5.0 out of 5 average rating, 173 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, 187 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
20–25 Sept
4.95 out of 5 average rating, 184 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, 32 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
2 bedrooms, 4 beds, 2 bathrooms
17–22 Aug
4.96 out of 5 average rating, 257 reviews
Guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed, 1 bathroom
16–21 Aug
4.96 out of 5 average rating, 133 reviews
Top guest favourite
Room in Stevensville
Rustic & Elegant Private Bed & Bath
1 bed, 1 bathroom
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, WC
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, 1 bathroom
20–25 Sept
4.9 out of 5 average rating, 361 reviews
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds, 1 bathroom
29 Nov – 4 Dec
4.97 out of 5 average rating, 457 reviews
Hotel in Annapolis
Close to U.S. Naval Academy + Breakfast. Pool. Gym
1 bedroom, 1 king bed, 1 bathroom
9–14 Aug
4.55 out of 5 average rating, 20 reviews
Guest favourite
Flat in Annapolis
Uptown Condo w 2 Parking Spots
1 bedroom, 1 bathroom
10–15 Aug
5.0 out of 5 average rating, 17 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
6–11 Sept
4.94 out of 5 average rating, 185 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, 252 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, 422 reviews
Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds, 2 bathrooms
18–23 Aug
4.96 out of 5 average rating, 113 reviews
Guest favourite
Rooms in Edgewater
Cheerful 2 bedroom shared home with water views
2 bedrooms, 2 queen beds, 1 bathroom
15–20 Aug
4.86 out of 5 average rating, 92 reviews
Top guest favourite
Home in Annapolis
Modern Annapolis Getaway - 2 Free Parking Spaces
2 bedrooms, 2 double beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 117 reviews