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Search results; Over 1,000 homes in Annapolis

Guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds, 1 private bathroom
20–25 Sept
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4.94 out of 5 average rating, 147 reviews
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, 15 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
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 Edgewater
3 BRs House+Patio+Playground
3 bedrooms, 3 beds
13–18 Sept
4.93 out of 5 average rating, 105 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, 146 reviews
Top guest favourite
Home in Annapolis
Charming on Charles Street
3 bedrooms, 4 beds
19–24 Sept
5.0 out of 5 average rating, 33 reviews
Guest favourite
Home in Annapolis
Beautiful house in the best location!
3 bedrooms, 6 beds
21–26 Sept
4.94 out of 5 average rating, 54 reviews
Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds
13–18 Sept
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Townhouse in Annapolis
Beautiful Downtown Annapolis Townhome!
3 bedrooms, 7 beds
13–18 Sept
5.0 out of 5 average rating, 119 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
Cozy Naptown Perch
2 bedrooms, 3 beds
29 Oct – 3 Nov
4.96 out of 5 average rating, 228 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
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 177 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed
25–30 Oct
4.9 out of 5 average rating, 122 reviews
Top guest favourite
Guest house in Annapolis
Garden View, 1 Bedroom and a Loft.
2 bedrooms, 3 beds
13–18 Sept
4.99 out of 5 average rating, 167 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, 462 reviews
Top guest favourite
Home in Annapolis
Quiet Waterfront
3 bedrooms, 3 beds
6–11 Dec
4.98 out of 5 average rating, 190 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds
1–6 Nov
4.92 out of 5 average rating, 1137 reviews