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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Apartment in Annapolis
Annapolis Condo-1 bedroom King
1 bedroom, 3 beds, 1 private bathroom
1–6 Aug
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4.97 out of 5 average rating, 126 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, 187 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
16–21 Aug
4.93 out of 5 average rating, 182 reviews
Top guest favourite
Room in Annapolis
Cozy Annapolis Retreat – Private Bedroom & Bath
1 queen bed
23–28 Aug
5.0 out of 5 average rating, 39 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, 183 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
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, 1128 reviews
Guest favourite
Flat in Annapolis
Annapolis Adventure 1 block to Harbor @ Gate 1
1 bedroom
9–14 Aug
5.0 out of 5 average rating, 12 reviews
Top 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, 39 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, 16 reviews
Top guest favourite
Room in Arnold
Beautiful bedroom, beautiful view near Annapolis
1 double bed
1–6 Aug
4.98 out of 5 average rating, 89 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
14–19 Aug
4.97 out of 5 average rating, 466 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 Edgewater
1 large room efficiency in detached garage.
1 bedroom, 1 queen bed
22–27 Aug
4.99 out of 5 average rating, 168 reviews
Top guest favourite
Room in Annapolis
Modern Suite with Spa Feel Near Downtown Annapolis
1 king bed
10–15 Aug
4.88 out of 5 average rating, 60 reviews
Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds
23–28 Aug
4.95 out of 5 average rating, 142 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, 419 reviews
Superhost
Home in Annapolis
Harbor’s Edge Retreat: Walk to Main St & Academy
3 bedrooms, 3 beds
2–7 Aug
4.89 out of 5 average rating, 84 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
24–29 Aug
4.98 out of 5 average rating, 62 reviews