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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds, 1 private bathroom
9–14 Sept
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4.95 out of 5 average rating, 142 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
23–28 Aug
4.93 out of 5 average rating, 190 reviews
Room in Bowie
Cozy Private Queen Room | Free Parking | Near DC
1 queen bed
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
29 Aug – 3 Sept
4.95 out of 5 average rating, 187 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, 135 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
13–18 Sept
4.94 out of 5 average rating, 187 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, 424 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
23–28 Aug
4.89 out of 5 average rating, 368 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds
16–21 Aug
4.97 out of 5 average rating, 97 reviews
Top guest favourite
Room in Annapolis
“Room at the Inn…”
1 queen bed
7–12 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Room in Annapolis
A Cottage Room in Presidents Hill
1 single bed
12–17 Sept
4.88 out of 5 average rating, 180 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds
17–22 Aug
4.93 out of 5 average rating, 60 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
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, 1132 reviews
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed
17–22 Oct
5.0 out of 5 average rating, 224 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
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed
23–28 Aug
4.91 out of 5 average rating, 115 reviews
Top guest favourite
Guest house in Edgewater
1 large room efficiency in detached garage.
1 bedroom, 1 queen bed
12–17 Sept
4.99 out of 5 average rating, 172 reviews
Hotel in Annapolis
Close to U.S. Naval Academy + Breakfast. Pool. Gym
1 bedroom, 1 king bed
16–21 Aug
4.61 out of 5 average rating, 23 reviews