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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, 103 reviews
Guest favorite
Cottage in Annapolis
Wright’s Cottage, Pets Welcome!
1 queen bed
Apr 2 – 7
4.94 out of 5 average rating, 307 reviews
Guest favorite
Guest suite in Annapolis
Annapolis Garden Suite
3 beds
Apr 1 – 6
4.94 out of 5 average rating, 67 reviews
Guest favorite
Townhouse in Annapolis
Historic 3 Bedroom Downtown Annapolis Townhome
5 beds
Apr 14 – 19
4.97 out of 5 average rating, 96 reviews
Guest favorite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 king beds
Apr 7 – 12
4.96 out of 5 average rating, 328 reviews
Guest favorite
Guesthouse in Glen Burnie
The Crab House - a Private, Waterfront Guest House
1 queen bed
Apr 7 – 12
4.94 out of 5 average rating, 259 reviews
Guest favorite
Home in Annapolis
New Hotel Chic
2 beds
May 5 – 10
4.95 out of 5 average rating, 340 reviews
Superhost
Condo in Annapolis
Charming Annapolis Waterfront Condo
3 beds
Apr 7 – 12
New place to stay
Guest favorite
Guesthouse in Stevensville
Waterfront Getaway - View of bay from your bed
1 queen bed
Apr 1 – 6
5.0 out of 5 average rating, 202 reviews
Guest favorite
Home in Annapolis
Chesapeake Comfort, Annapolis.
4 beds
Apr 19 – 24
4.97 out of 5 average rating, 130 reviews
Guest favorite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
4 beds
Apr 1 – 6
4.96 out of 5 average rating, 98 reviews
Guest favorite
Home in Annapolis
Charming Annapolis Retreat with Hidden Wine Room
3 beds
Apr 27 – May 2
4.96 out of 5 average rating, 27 reviews
Guest favorite
Home in Annapolis
Historic Downtown House with Off Street Parking
5 beds
Apr 14 – 19
4.91 out of 5 average rating, 81 reviews
Guest favorite
Houseboat in Stevensville
Chesapeake Houseboat Getaway
3 beds
Apr 14 – 19
4.96 out of 5 average rating, 26 reviews
Guest favorite
Cottage in Annapolis
Waterfront farm retreat for vacation & telework
4 beds
Apr 1 – 6
4.97 out of 5 average rating, 114 reviews
Superhost
Home in Annapolis
USNA Luxury Home in Downtown Annapolis w/parking!
12 beds
Apr 2 – 7
5.0 out of 5 average rating, 4 reviews
Guest favorite
Home in Annapolis
Gorgeous Historic Downtown Annapolis House
9 beds
Apr 1 – 6
4.97 out of 5 average rating, 112 reviews
Home in Annapolis
Sail into your Waterfront Oasis in Annapolis!
5 beds
Apr 1 – 6
New place to stay