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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
30 Aug – 4 Sept
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4.97 out of 5 average rating, 470 reviews
Home in Annapolis
Gracie's Gallery & Garden in Annapolis
4 bedrooms, 6 beds
21–26 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds
28 Aug – 2 Sept
4.92 out of 5 average rating, 61 reviews
Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed
20–25 Aug
4.9 out of 5 average rating, 50 reviews
Guest favourite
Guest house in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 bedroom, 1 queen bed
21–26 Aug
4.95 out of 5 average rating, 210 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
13–18 Sept
4.94 out of 5 average rating, 189 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
23–28 Aug
4.93 out of 5 average rating, 191 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
23–28 Aug
4.89 out of 5 average rating, 369 reviews
Hotel room in Annapolis
Governor Calvert King | Historic Inns
1 bedroom, 1 king bed
23–28 Aug
4.62 out of 5 average rating, 37 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
1–6 Sept
4.98 out of 5 average rating, 163 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed
30 Aug – 4 Sept
4.91 out of 5 average rating, 116 reviews
Top guest favourite
Guest house in Annapolis
Guesthouse on The Weems Creek
1 bedroom, 1 queen bed
21–26 Aug
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds
20–25 Sept
4.97 out of 5 average rating, 97 reviews
Top guest favourite
Room in Severna Park
Severna Park Private Entry Suite
2 beds
20–25 Aug
4.98 out of 5 average rating, 64 reviews
Top guest favourite
Guest house in Annapolis
Walk to City Dock & USNA | Designer Eastport Home
2 bedrooms, 3 beds
20–25 Aug
4.98 out of 5 average rating, 44 reviews
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms, 6 beds
24–29 Aug
4.94 out of 5 average rating, 32 reviews
Guest favourite
Room in Annapolis
Laura’s Room
1 double bed
21–26 Aug
4.88 out of 5 average rating, 93 reviews
Guest favourite
Guest suite in Arnold
Captains Quarters Oasis Near Annapolis, Sleeps 4
1 bedroom, 2 beds
24–29 Aug
4.95 out of 5 average rating, 213 reviews
Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
3 bedrooms, 5 beds
21–26 Aug
4.99 out of 5 average rating, 69 reviews