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Search results; Over 1,000 places

Superhost
Apartment in Annapolis
Modern Apartment over the Heart of Main Street!
1 min walk
Jul 21 – 26
4.82 out of 5 average rating, 655 reviews
Superhost
Home in Annapolis
Historic Luxury Steps to USNA + Vibrant Waterfront
4 min walk
Apr 21 – 26
New place to stay
Guest favorite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 min walk
Jun 18 – 23
4.91 out of 5 average rating, 916 reviews
Guest favorite
Home in Annapolis
Boutique Historic Home Steps from the State House!
2 min walk
Apr 21 – 26
4.99 out of 5 average rating, 83 reviews
Guest favorite
Guest suite in Annapolis
Charming 18th C. Apt in DTA
2 min walk
Apr 21 – 26
4.89 out of 5 average rating, 79 reviews
Guest favorite
Apartment in Annapolis
LOCATION!! Steps away from historic Main Street.
3 min walk
Apr 29 – May 4
5.0 out of 5 average rating, 66 reviews
Guest favorite
Townhouse in Annapolis
Beautiful Downtown Annapolis Home!
1 min walk
Apr 28 – May 3
4.98 out of 5 average rating, 91 reviews
Guest favorite
Home in Annapolis
Villa Annapolitana • Parking 1 min • USNA 4 min
2 min walk
Apr 28 – May 3
4.96 out of 5 average rating, 50 reviews
Guest favorite
Cottage in Annapolis
Secluded Cozy Cottage in Historic Downtown
2 min walk
Apr 19 – 24
4.94 out of 5 average rating, 172 reviews
Guest favorite
Home in Annapolis
Fleet St downtown with garage parking and EV
2 min walk
Apr 28 – May 3
5.0 out of 5 average rating, 20 reviews
Superhost
Home in Annapolis
Downtown Pinkney House w/Parking
4 min walk
Apr 19 – 24
New place to stay
Guest favorite
Home in Annapolis
East Street Retreat
3 min walk
Apr 29 – May 4
5.0 out of 5 average rating, 6 reviews
Guest favorite
Room in Annapolis
Rooms at Garden House next to USNA & Harbor
4 min walk
May 27 – Jun 1
4.96 out of 5 average rating, 203 reviews
Guest favorite
Home in Annapolis
Quiet Waterfront
3 min walk
Aug 25 – 30
4.98 out of 5 average rating, 155 reviews
Guest favorite
Home in Annapolis
Historic Downtown in-law suite
5 min walk
Nov 18 – 23
4.96 out of 5 average rating, 108 reviews
Guest favorite
Home in Annapolis
Elegant & Authentic Annapolis
4 min walk
Apr 28 – May 3
5.0 out of 5 average rating, 37 reviews
Guest favorite
Townhouse in Annapolis
Centrally Located, Charming Historic Townhouse
2 min walk
Jul 9 – 14
4.97 out of 5 average rating, 158 reviews
Guest favorite
Home in Annapolis
Green On Fleet - Rowhouse in Historic Annapolis
3 min walk
Jun 3 – 8
4.96 out of 5 average rating, 75 reviews