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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 beds, 1 private bathroom
14–19 Aug
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4.97 out of 5 average rating, 463 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
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 bathroom
2–7 Aug
5.0 out of 5 average rating, 38 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
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, 3 bathrooms
15–20 Aug
4.95 out of 5 average rating, 182 reviews
Top guest favourite
Home in Annapolis
Annapolis Charm –Bright 3BR in Downtown
3 bedrooms, 6 beds, 2 bathrooms
9–14 Aug
4.92 out of 5 average rating, 132 reviews
Guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Aug
4.97 out of 5 average rating, 38 reviews
Top guest favourite
Guest house in Edgewater
1 large room efficiency in detached garage.
1 bedroom, 1 queen bed, 1 bathroom
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, 2 bathrooms
1–6 Aug
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Home in Annapolis
Bungalow Basement in Annapolis
1 bedroom, 4 beds, 1 bathroom
1–6 Aug
4.9 out of 5 average rating, 50 reviews
Top guest favourite
Guest house in Annapolis
Eastport Gem ~ Walk to Downtown Annapolis
1 bedroom, 2 beds, 1.5 bathrooms
10–15 Aug
5.0 out of 5 average rating, 93 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.92 out of 5 average rating, 1127 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed, 1 bathroom
1–6 Aug
4.98 out of 5 average rating, 161 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Room in Annapolis
“Room at the Inn…”
1 queen bed, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
1 queen bed, 1 bathroom
17–22 Aug
4.96 out of 5 average rating, 417 reviews
Guest favourite
Apartment in Annapolis
Semper Fi Condo
2 bedrooms, 3 queen beds, 2 bathrooms
2–7 Aug
4.89 out of 5 average rating, 18 reviews
Top guest favourite
Home in Annapolis
Elegant & Authentic Annapolis
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 152 reviews
Top guest favourite
Room in Arnold
Beautiful bedroom, beautiful view near Annapolis
1 double bed, 1.5 bathrooms
1–6 Aug
4.98 out of 5 average rating, 88 reviews