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Search results; Over 1,000 homes in Annapolis

Guest favourite
Home in Cape St. Claire
Country House on the Bay
5 bedrooms, 10 beds, 3 private bathrooms
14–19 Sept
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4.9 out of 5 average rating, 228 reviews
Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4 bedrooms, 6 beds
4–9 Oct
4.96 out of 5 average rating, 47 reviews
Top guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds
13–18 Sept
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds
3–8 Dec
4.97 out of 5 average rating, 461 reviews
Guest favourite
Home in Annapolis
Admiral’s Landing: Walk to Naval Academy, West St.
3 bedrooms, 3 beds
13–18 Sept
4.98 out of 5 average rating, 53 reviews
Guest favourite
Home in Annapolis
Waterfront Oasis in Eastport-Easy Walk to Downtown
5 bedrooms, 8 beds
13–18 Sept
4.93 out of 5 average rating, 124 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds
20–25 Sept
4.91 out of 5 average rating, 92 reviews
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds
25–30 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds
7–12 Sept
4.95 out of 5 average rating, 146 reviews
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
2 bedrooms, 4 beds
13–18 Sept
4.87 out of 5 average rating, 77 reviews
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
20–25 Sept
4.97 out of 5 average rating, 66 reviews
Guest favourite
Home in Annapolis
Across from stadium - walk to downtown Annapolis!
4 bedrooms, 4 beds
13–18 Sept
4.9 out of 5 average rating, 136 reviews
Top guest favourite
Home in Annapolis
4 bedrooms, 7 beds, 3 bath completely updated
4 bedrooms, 7 beds
11–16 Oct
4.97 out of 5 average rating, 145 reviews
Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds
7–12 Sept
5.0 out of 5 average rating, 52 reviews
Guest favourite
Home in Annapolis
Beautiful house in the best location!
3 bedrooms, 6 beds
13–18 Sept
4.94 out of 5 average rating, 52 reviews
Top guest favourite
Home in Annapolis
Eastport Oasis
5 bedrooms, 5 beds
1–6 Nov
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Home in Annapolis
Historic & sunny home steps from USNA/downtown
3 bedrooms, 5 beds
29 Nov – 4 Dec
5.0 out of 5 average rating, 202 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
3–8 Oct
4.97 out of 5 average rating, 470 reviews
Top guest favourite
Guest suite in Annapolis
Cozy Naptown Perch
2 bedrooms, 3 beds
29 Oct – 3 Nov
4.96 out of 5 average rating, 227 reviews