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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Annapolis
Elegant & Authentic Annapolis
1 bedroom, 1 bed, 1 private bathroom
20–25 Sept
,
4.99 out of 5 average rating, 157 reviews
Top guest favourite
Home in Edgewater
3 BRs House+Patio+Playground
3 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
4.93 out of 5 average rating, 104 reviews
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Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 22 reviews
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Townhouse in Annapolis
Beautiful Downtown Annapolis Townhome!
3 bedrooms, 7 beds, 3.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 119 reviews
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Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 146 reviews
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Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds, 2.5 bathrooms
26 Sept – 1 Oct
4.98 out of 5 average rating, 42 reviews
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Home in Annapolis
The Red Door Cottage - Pet-Friendly!
2 bedrooms, 2 beds, 2 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 41 reviews
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Home in Annapolis
West street historic home
5 bedrooms, 6 beds, 3 bathrooms
7–12 Sept
4.97 out of 5 average rating, 72 reviews
Guest favourite
Home in Annapolis
Charming 5BR Naptown Home <1 Mile to Stadium
5 bedrooms, 9 beds, 3.5 bathrooms
13–18 Sept
4.99 out of 5 average rating, 71 reviews
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Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 52 reviews
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Home in Annapolis
Charming on Charles Street
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 33 reviews
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Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds, 3.5 bathrooms
20–25 Sept
4.91 out of 5 average rating, 92 reviews
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Home in Annapolis
Historic & sunny home steps from USNA/downtown
3 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 202 reviews
Top guest favourite
Home in Annapolis
3BR/2BA Annapolis Cottage
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.98 out of 5 average rating, 226 reviews
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
2 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
4.87 out of 5 average rating, 77 reviews
Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4 bedrooms, 6 beds, 3.5 bathrooms
6–11 Sept
4.96 out of 5 average rating, 47 reviews
Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
4.99 out of 5 average rating, 69 reviews
Top guest favourite
Home in Annapolis
Eastport Oasis
5 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
4.97 out of 5 average rating, 64 reviews