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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
1–6 Aug
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5.0 out of 5 average rating, 172 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
4.93 out of 5 average rating, 181 reviews, 1 queen bed, 1.5 bathrooms
16–21 Aug
Top guest favourite
Room in Annapolis
Cozy Annapolis Retreat – Private Bedroom & Bath
5.0 out of 5 average rating, 37 reviews, 1 queen bed, 1 bathroom
1–6 Aug
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
4.93 out of 5 average rating, 186 reviews, 1 queen bed, 1.5 bathrooms
10–15 Aug
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
4.95 out of 5 average rating, 182 reviews, 1 queen bed, 3 bathrooms
15–20 Aug
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
4.92 out of 5 average rating, 1127 reviews, 1 bedroom, 2 beds, 1 bathroom
20–25 Sept
Guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
4.97 out of 5 average rating, 38 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Aug
Top guest favourite
Home in Annapolis
Annapolis Charm –Bright 3BR in Downtown
4.92 out of 5 average rating, 132 reviews, 3 bedrooms, 6 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Home in Annapolis
Bungalow Basement in Annapolis
4.9 out of 5 average rating, 50 reviews, 1 bedroom, 4 beds, 1 bathroom
1–6 Aug
Top guest favourite
Guest house in Edgewater
1 large room efficiency in detached garage.
4.99 out of 5 average rating, 168 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Superhost
Home in Annapolis
Cozy Cottage w/ Beach Access Near Annapolis
4.93 out of 5 average rating, 14 reviews, 2 bedrooms, 3 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
4.98 out of 5 average rating, 161 reviews, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
5.0 out of 5 average rating, 14 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
Top guest favourite
Guest house in Annapolis
Eastport Gem ~ Walk to Downtown Annapolis
5.0 out of 5 average rating, 93 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
10–15 Aug
Top guest favourite
Room in Annapolis
“Room at the Inn…”
5.0 out of 5 average rating, 31 reviews, 1 queen bed, 1 bathroom
1–6 Aug
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
4.96 out of 5 average rating, 417 reviews, 1 queen bed, 1 bathroom
17–22 Aug
Guest favourite
Flat in Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
4.92 out of 5 average rating, 520 reviews, 1 bedroom, 2 beds, 1 bathroom
11–16 Aug
Top guest favourite
Home in Annapolis
Elegant & Authentic Annapolis
4.99 out of 5 average rating, 152 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Top guest favourite
Home in Pasadena
Waterfront CHeerful 2 with Private home
4.98 out of 5 average rating, 97 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
17–22 Oct