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Search results; Over 1,000 homes in Annapolis

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
Annapolis Charm –Bright 3BR in Downtown
3 bedrooms, 6 beds
20–25 Sept
4.93 out of 5 average rating, 137 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 22 reviews
Flat in Annapolis
Prime Eastport Location-10 Min Walk to City Dock
1 bedroom, 1 queen bed
11–16 Oct
New place to stay
Superhost
Home in Annapolis
Annapolis Charmer - Perfect Location
3 bedrooms, 3 beds
27 Sept – 2 Oct
New place to stay
Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 52 reviews
Guest favourite
Home in Annapolis
Across from stadium - walk to downtown Annapolis!
4 bedrooms, 4 beds
4–9 Oct
4.9 out of 5 average rating, 136 reviews
Top guest favourite
Home in Annapolis
The Red Door Cottage - Pet-Friendly!
2 bedrooms, 2 beds
29 Nov – 4 Dec
5.0 out of 5 average rating, 43 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
Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds
21–26 Sept
New place to stay
Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
3 bedrooms, 5 beds
28 Sept – 3 Oct
4.99 out of 5 average rating, 70 reviews
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Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds
20–25 Sept
5.0 out of 5 average rating, 147 reviews
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Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds
3–8 Dec
4.97 out of 5 average rating, 463 reviews
Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds
26 Sept – 1 Oct
4.98 out of 5 average rating, 44 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, 203 reviews
Top guest favourite
Home in Annapolis
Welcoming Luxury Estate for Family, Friends, Pets
7 bedrooms, 6 beds
27 Oct – 1 Nov
5.0 out of 5 average rating, 30 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
Historic Downtown in-law suite
1 bedroom, 2 beds
4–9 Dec
4.96 out of 5 average rating, 265 reviews