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Search results; Over 1,000 places in Annapolis

Guest favorite
Room in Annapolis
Stay with JenniferHosting for 6 years,
Chesapeake Mornings
Apr 21 – 26
4.96 out of 5 average rating, 451 reviews
Superhost
Home in Annapolis
Historic Luxury Steps to USNA + Vibrant Waterfront
6 beds
Apr 1 – 6
New place to stay
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
Guesthouse in Annapolis
Calico Cottage Guest House, king bed, free parking
1 king bed
Apr 7 – 12
4.9 out of 5 average rating, 202 reviews
Guest favorite
Guesthouse in Annapolis
Coastal Waterfront 1 Bedroom Cottage
Apr 1 – 6
4.99 out of 5 average rating, 102 reviews
Superhost
Apartment in Annapolis
Modern Apartment over the Heart of Main Street!
2 queen beds
Jul 21 – 26
4.82 out of 5 average rating, 645 reviews
Guest favorite
Guest suite in Arnold
Old Bay Bungalow
2 beds
Apr 6 – 11
4.96 out of 5 average rating, 560 reviews
Home in Annapolis
Quaint in the Heart of Annapolis
2 queen beds
Apr 1 – 6
New place to stay
Guest favorite
Condo in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
2 beds
Apr 10 – 15
4.96 out of 5 average rating, 208 reviews
Guest favorite
Room in Annapolis
Stay with Michael
Front Room - Private room in Annapolis
Apr 1 – 6
4.9 out of 5 average rating, 79 reviews
Guest favorite
Apartment in Annapolis
Eastport Bungalow
1 queen bed
Apr 1 – 6
4.92 out of 5 average rating, 59 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
Condo in Annapolis
1 Bedroom Apt - Walk to Downtown - With Parking
2 beds
Apr 1 – 6
4.94 out of 5 average rating, 49 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
Apartment in Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
2 beds
Apr 1 – 6
4.92 out of 5 average rating, 439 reviews
Guest favorite
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
2 beds
Apr 12 – 17
4.94 out of 5 average rating, 349 reviews
Guest favorite
Home in Annapolis
Historic & sunny home steps from USNA/downtown
5 beds
Apr 7 – 12
5.0 out of 5 average rating, 82 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