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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Annapolis
Beach Access, Hot Tub, Pet Friendly, Fully Fenced
4 bedrooms, 4 beds, 2.5 private bathrooms
13–18 Sept
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4.99 out of 5 average rating, 140 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, 188 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
Room in Annapolis
“Room at the Inn…”
1 queen bed
16–21 Aug
5.0 out of 5 average rating, 32 reviews
Hotel room in Annapolis
Historic Inn Stay | Steps from Maryland State
1 bedroom, 1 double bed
10–15 Aug
5.0 out of 5 average rating, 4 reviews
Room in Bowie
Cozy Private Queen Room | Free Parking | Near DC
1 queen bed
17–22 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Room in Annapolis
A Cottage Room in Presidents Hill
1 single bed
15–20 Aug
4.88 out of 5 average rating, 180 reviews
Guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed
16–21 Aug
4.96 out of 5 average rating, 133 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds
10–15 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
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
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
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
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 31 reviews
Guest favourite
Room in Annapolis
Kingfisher Room - Private Room w/ Bath, Annapolis
1 queen bed
12–17 Aug
5.0 out of 5 average rating, 39 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
Hotel in Annapolis
Close to U.S. Naval Academy + Breakfast. Pool. Gym
1 bedroom, 1 king bed
10–15 Aug
4.57 out of 5 average rating, 21 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
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