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Search results; Over 1,000 places in Annapolis

Guest favorite
Home in Annapolis
Historic Downtown in-law suite
1 bed
Nov 18 – 23
4.96 out of 5 average rating, 109 reviews
Guest favorite
Home in Annapolis
Historic & sunny home steps from USNA/downtown
5 beds
May 19 – 24
5.0 out of 5 average rating, 84 reviews
Guest favorite
Home in Annapolis
Cozy 2br home w/ parking in downtown Annapolis
3 beds
Apr 20 – 25
4.94 out of 5 average rating, 287 reviews
Guest favorite
Home in Annapolis
Villa Annapolitana • Parking 1 min • USNA 4 min
3 beds
Apr 28 – May 3
4.96 out of 5 average rating, 50 reviews
Home in Annapolis
Quaint in the Heart of Annapolis
Apr 28 – May 3
New place to stay
Guest favorite
Home in Annapolis
Chesapeake Comfort, Annapolis.
4 beds
May 5 – 10
4.97 out of 5 average rating, 132 reviews
Guest favorite
Home in Annapolis
Adorable 1 bedroom apartment in downtown Annapolis
2 beds
Apr 21 – 26
4.87 out of 5 average rating, 46 reviews
Guest favorite
Home in Edgewater
Annapolis Area Waterside Retreat
4 queen beds
May 5 – 10
4.95 out of 5 average rating, 97 reviews
Guest favorite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
4 beds
Apr 21 – 26
4.96 out of 5 average rating, 102 reviews
Guest favorite
Home in Annapolis
Elegant & Authentic Annapolis
1 queen bed
Apr 28 – May 3
5.0 out of 5 average rating, 37 reviews
Guest favorite
Home in Annapolis
New Hotel Chic
2 beds
Jun 9 – 14
4.95 out of 5 average rating, 345 reviews
Home in Annapolis
Nautical - and oh, so nice!
4 beds
Apr 20 – 25
New place to stay
Guest favorite
Home in Annapolis
Green On Fleet - Rowhouse in Historic Annapolis
2 beds
Jun 3 – 8
4.96 out of 5 average rating, 75 reviews
Superhost
Home in Annapolis
Historic Luxury Steps to USNA + Vibrant Waterfront
6 beds
Apr 21 – 26
New place to stay
Superhost
Home in Annapolis
Downtown Pinkney House w/Parking
2 queen beds
Apr 20 – 25
New place to stay
Guest favorite
Home in Annapolis
Charming Annapolis Retreat with Hidden Wine Room
3 beds
May 5 – 10
4.97 out of 5 average rating, 31 reviews
Guest favorite
Home in Annapolis
Charming house; walk to everywhere in Annapolis
2 beds
May 1 – 6
4.99 out of 5 average rating, 145 reviews
Guest favorite
Home in Annapolis
The Naval Nook 1.3 mi. from Downtown Annapolis
4 beds
Apr 28 – May 3
4.95 out of 5 average rating, 56 reviews