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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Waterfront farm retreat for vacation & telework
3 bedrooms, 5 beds, 1.5 shared bathrooms
1–6 Nov
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4.98 out of 5 average rating, 161 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, 181 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
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
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
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds
23–28 Aug
4.95 out of 5 average rating, 142 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
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds
15–20 Aug
4.97 out of 5 average rating, 39 reviews
Superhost
Flat in Annapolis
Walk to Navy Stadium | Private Studio w/ Parking
1 bedroom, 1 queen bed
1–6 Aug
New place to stay
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, 88 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
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
Cape Cod Charm close to USNA & Annapolis - Room 2
1 queen bed
10–15 Aug
4.96 out of 5 average rating, 419 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
24–29 Aug
4.98 out of 5 average rating, 62 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
Studio Apt. Historic Annapolis
1 bedroom, 1 bed
2–7 Aug
4.87 out of 5 average rating, 23 reviews
Guest favourite
Flat in Annapolis
Spa Creek Condo | Pool, Deck & Parking
1 bedroom, 2 beds
1–6 Aug
5.0 out of 5 average rating, 14 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