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Search results; Over 1,000 homes in Annapolis

Guest favourite
Flat in Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
1 bedroom, 2 beds, 1 private bathroom
16–21 Aug
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4.92 out of 5 average rating, 520 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 30 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
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed
20–25 Sept
4.95 out of 5 average rating, 184 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds
15–20 Aug
4.96 out of 5 average rating, 77 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds
16–21 Aug
4.97 out of 5 average rating, 97 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
23–28 Aug
4.93 out of 5 average rating, 84 reviews
Guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
3 bedrooms, 4 beds
16–21 Aug
4.94 out of 5 average rating, 202 reviews
Guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
4 bedrooms, 6 beds
10–15 Aug
4.92 out of 5 average rating, 25 reviews
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
2 bedrooms, 6 beds
16–21 Aug
4.92 out of 5 average rating, 25 reviews
Top guest favourite
Guest house in Edgewater
1 large room efficiency in detached garage.
1 bedroom, 1 queen bed
12–17 Sept
4.99 out of 5 average rating, 170 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
24–29 Aug
4.98 out of 5 average rating, 63 reviews
Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
3 bedrooms, 5 beds
10–15 Aug
4.99 out of 5 average rating, 68 reviews
Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed
9–14 Aug
4.89 out of 5 average rating, 47 reviews
Top guest favourite
Home in Annapolis
Newly Renovated Downtown Charm, Game Room, Patio
2 bedrooms, 3 beds
9–14 Aug
5.0 out of 5 average rating, 33 reviews
Guest favourite
Rooms in Edgewater
Cheerful 2 bedroom shared home with water views
2 bedrooms, 2 queen beds
15–20 Aug
4.86 out of 5 average rating, 92 reviews
Top guest favourite
Flat in Annapolis
Beautiful Historic Home next to City Dock + USNA
3 bedrooms, 4 beds
14–19 Aug
5.0 out of 5 average rating, 57 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds
30 Sept – 5 Oct
5.0 out of 5 average rating, 21 reviews
Guest favourite
Home in Annapolis
Stay Retro Naptown
4 bedrooms, 4 queen beds
15–20 Sept
4.95 out of 5 average rating, 80 reviews