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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Townhouse in Annapolis
Moose’s Happy Place
3 bedrooms, 4 beds, 3.5 shared bathrooms
25–30 Nov
,
5.0 out of 5 average rating, 113 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, 184 reviews
Room in Bowie
Cozy Private Queen Room | Free Parking | Near DC
1 queen bed
17–22 Aug
New place to stay
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
Top guest favourite
Room in Annapolis
“Room at the Inn…”
1 queen bed
9–14 Aug
5.0 out of 5 average rating, 32 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 king bed
16–21 Aug
4.9 out of 5 average rating, 360 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, 185 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 30 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
10–15 Aug
4.89 out of 5 average rating, 366 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
5–10 Aug
4.98 out of 5 average rating, 162 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds
6–11 Aug
4.93 out of 5 average rating, 59 reviews
Guest favourite
Room in Annapolis
Laura’s Room
1 double bed
5–10 Aug
4.88 out of 5 average rating, 93 reviews
Top guest favourite
Room in Stevensville
Rustic & Elegant Private Bed & Bath
1 bed
9–14 Aug
4.98 out of 5 average rating, 304 reviews
Top guest favourite
Home in Annapolis
Modern Annapolis Getaway - 2 Free Parking Spaces
2 bedrooms, 2 double beds
16–21 Aug
5.0 out of 5 average rating, 117 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds
1–6 Nov
4.92 out of 5 average rating, 1128 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
Top guest favourite
Guest house in Annapolis
Private Art-Filled Guesthouse near Naval Academy
1 bed
16–21 Aug
5.0 out of 5 average rating, 173 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