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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed
25–30 Oct
4.91 out of 5 average rating, 121 reviews
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
20–25 Sept
4.97 out of 5 average rating, 66 reviews
Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds
10–15 Sept
5.0 out of 5 average rating, 52 reviews
Guest favourite
Home in Annapolis
Stay Retro Naptown
4 bedrooms, 4 queen beds
9–14 Nov
4.94 out of 5 average rating, 86 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, 42 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
West street historic home
5 bedrooms, 6 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 73 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
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
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
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds
10–15 Sept
5.0 out of 5 average rating, 147 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
Top guest favourite
Home in Annapolis
3BR/2BA Annapolis Cottage
3 bedrooms, 4 beds
10–15 Sept
4.98 out of 5 average rating, 226 reviews
Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds
1–6 Jan
4.96 out of 5 average rating, 262 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, 43 reviews
Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
3 bedrooms, 5 beds
10–15 Sept
4.99 out of 5 average rating, 69 reviews
Guest suite in Annapolis
Annapolis Home 5 miles from Downtown Annapolis
4 bedrooms, 4 beds
13–18 Sept
New place to stay
Guest favourite
Home in Annapolis
Cute bungalow blocks to Stadium
2 bedrooms, 3 beds
11–16 Sept
4.95 out of 5 average rating, 81 reviews