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Search results; Over 1,000 places in Annapolis

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Guest favorite
Guesthouse in Annapolis
Calico Cottage Guest House, king bed, free parking
1 king bed
Jul 7 – 12
4.9 out of 5 average rating, 206 reviews
Guest favorite
Condo in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
2 beds
Apr 21 – 26
4.96 out of 5 average rating, 213 reviews
Superhost
Apartment in Annapolis
Modern Apartment over the Heart of Main Street!
Professional Host
Jul 21 – 26
4.82 out of 5 average rating, 656 reviews
Guest favorite
Guest suite in Arnold
Old Bay Bungalow
Individual Host
Apr 28 – May 3
4.96 out of 5 average rating, 563 reviews
Guest favorite
Home in Annapolis
Historic Downtown in-law suite
1 bed
Nov 18 – 23
4.96 out of 5 average rating, 108 reviews
Guest favorite
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
Individual Host
Apr 21 – 26
4.94 out of 5 average rating, 351 reviews
Guest favorite
Cottage in Annapolis
Wright’s Cottage, Pets Welcome!
Individual Host
Apr 21 – 26
4.94 out of 5 average rating, 312 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
Guest favorite
Guesthouse in Annapolis
RECENTLY RENOVATED Cottage Near Downtown Annapolis
Individual Host
Apr 22 – 27
4.97 out of 5 average rating, 197 reviews
Guest favorite
Guesthouse in Annapolis
Annapolis Guesthouse - Completely Separate Space
Individual Host
Apr 21 – 26
4.91 out of 5 average rating, 174 reviews
Guest favorite
Guesthouse in Annapolis
Coastal Waterfront 1 Bedroom Cottage
Apr 21 – 26
4.99 out of 5 average rating, 104 reviews
Guest favorite
Home in Annapolis
Cozy 2br home w/ parking in downtown Annapolis
Professional Host
Apr 20 – 25
4.94 out of 5 average rating, 287 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, 101 reviews
Home in Annapolis
Quaint in the Heart of Annapolis
Individual Host
Apr 28 – May 3
New place to stay
Guest favorite
Home in Annapolis
New Hotel Chic
2 beds
Jun 9 – 14
4.95 out of 5 average rating, 344 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
Home in Annapolis
Nautical - and oh, so nice!
Individual Host
Apr 20 – 25
New place to stay
Guest favorite
Apartment in Annapolis
LOCATION!! Steps away from historic Main Street.
Individual Host
Apr 29 – May 4
5.0 out of 5 average rating, 66 reviews