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Search results; Over 1,000 homes in Annapolis

Guest favourite
Apartment in Annapolis
Capts Qrtrs - Awesome downtown Annapolis location!
1 bedroom, 1 bed, 1 private bathroom
9–14 Aug
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4.86 out of 5 average rating, 182 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 74 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
16–21 Jul
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
4.99 out of 5 average rating, 157 reviews, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
4.95 out of 5 average rating, 133 reviews, 2 bedrooms, 3 beds, 1 bathroom
20–25 Jul
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
4.95 out of 5 average rating, 180 reviews, 1 queen bed, 3 bathrooms
26–31 Jul
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
4.97 out of 5 average rating, 461 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Aug
Top guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
5.0 out of 5 average rating, 21 reviews, 4 bedrooms, 6 beds, 2.5 bathrooms
23–28 Jul
Guest favourite
Home in Annapolis
1 Block to USNA Stadium: Modern Annapolis Home!
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
4.93 out of 5 average rating, 179 reviews, 1 queen bed, 1.5 bathrooms
19–24 Jul
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment
4.9 out of 5 average rating, 104 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Guest house in Annapolis
Private Art-Filled Guesthouse near Naval Academy
5.0 out of 5 average rating, 171 reviews, 1 bed, 1 bathroom
7–12 Jul
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
13–18 Jul
Top guest favourite
Home in Annapolis
CJ's Cottage
4.96 out of 5 average rating, 72 reviews, 2 bedrooms, 3 beds, 2 bathrooms
11–16 Jul
Guest favourite
Home in Annapolis
Admiral’s Landing: Walk to Naval Academy, West St.
4.98 out of 5 average rating, 43 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
12–17 Jul
Superhost
Flat in Annapolis
Charming Eastport
4.77 out of 5 average rating, 297 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Jul
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
5.0 out of 5 average rating, 13 reviews, 4 bedrooms, 6 beds, 3 bathrooms
12–17 Sept
Hotel room in Annapolis
Governor Calvert King | Historic Inns
4.55 out of 5 average rating, 31 reviews, 1 bedroom, 1 bathroom
10–15 Jul
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
4.95 out of 5 average rating, 221 reviews, 1 bedroom, 1 bed, 1 bathroom
7–12 Jul
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
4.86 out of 5 average rating, 72 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
19–24 Jul