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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
1 queen bed
4–9 Aug
4.93 out of 5 average rating, 181 reviews
Top guest favourite
Room in Annapolis
Cozy Annapolis Retreat – Private Bedroom & Bath
1 queen bed
1–6 Aug
5.0 out of 5 average rating, 37 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
10–15 Aug
4.93 out of 5 average rating, 186 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed
15–20 Aug
4.95 out of 5 average rating, 182 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds
20–25 Sept
4.92 out of 5 average rating, 1127 reviews
Guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds
15–20 Aug
4.97 out of 5 average rating, 38 reviews
Top guest favourite
Home in Annapolis
Annapolis Charm –Bright 3BR in Downtown
3 bedrooms, 6 beds
1–6 Aug
4.92 out of 5 average rating, 132 reviews
Top guest favourite
Guest house in Edgewater
1 large room efficiency in detached garage.
1 bedroom, 1 queen bed
2–7 Aug
4.99 out of 5 average rating, 168 reviews
Superhost
Home in Annapolis
Cozy Cottage w/ Beach Access Near Annapolis
2 bedrooms, 3 beds
1–6 Aug
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds
15–20 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Annapolis
Bungalow Basement in Annapolis
1 bedroom, 4 beds
1–6 Aug
4.9 out of 5 average rating, 50 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
1–6 Aug
4.98 out of 5 average rating, 161 reviews
Top guest favourite
Room in Annapolis
“Room at the Inn…”
1 queen bed
1–6 Aug
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Guest house in Annapolis
Eastport Gem ~ Walk to Downtown Annapolis
1 bedroom, 2 beds
10–15 Aug
5.0 out of 5 average rating, 93 reviews
Top guest favourite
Guest house in Annapolis
"The Perch" - Hot Tub - Beach - Chesapeake Bay
1 bedroom, 1 queen bed
9–14 Aug
4.91 out of 5 average rating, 96 reviews
Top guest favourite
Home in Pasadena
Waterfront CHeerful 2 with Private home
2 bedrooms, 2 beds
17–22 Oct
4.98 out of 5 average rating, 97 reviews
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
1 queen bed
17–22 Aug
4.96 out of 5 average rating, 417 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
24–29 Aug
4.98 out of 5 average rating, 60 reviews