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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
Studio, 1 bed, 1 private bathroom
13–18 Sept
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4.98 out of 5 average rating, 165 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, 15 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
Guest suite in Annapolis
Cozy Naptown Perch
2 bedrooms, 3 beds
29 Oct – 3 Nov
4.96 out of 5 average rating, 227 reviews
Guest favourite
Flat in Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
1 bedroom, 3 beds
12–17 Sept
4.92 out of 5 average rating, 524 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
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
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
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
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
Top guest favourite
Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
2 bedrooms, 4 beds
13–18 Sept
4.97 out of 5 average rating, 258 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
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
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
20–25 Sept
4.93 out of 5 average rating, 194 reviews
Superhost
Home in Annapolis
Mast & Main | Steps to City Dock & Naval Academy
3 bedrooms, 3 beds
20–25 Sept
New place to stay
Guest favourite
Guest suite in Arnold
Captains Quarters Oasis Near Annapolis, Sleeps 4
1 bedroom, 2 beds
13–18 Sept
4.95 out of 5 average rating, 215 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
Apartment in Annapolis
Funky Uptown Apt meets Downtown - Hist District
2 bedrooms, 2 double beds
10–15 Sept
4.96 out of 5 average rating, 127 reviews
Guest favourite
Home in Annapolis
Charming Renovated Historic Home Downtown wParking
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.91 out of 5 average rating, 242 reviews