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Search results; Over 1,000 places in Annapolis

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
Home in Annapolis
Villa Annapolitana • Parking 1 min • USNA 4 min
3 beds
Apr 28 – May 3
4.96 out of 5 average rating, 49 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, 655 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
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
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
2 beds
Apr 21 – 26
4.94 out of 5 average rating, 351 reviews
Guest favorite
Guesthouse in Annapolis
RECENTLY RENOVATED Cottage Near Downtown Annapolis
1 king bed
Apr 22 – 27
4.97 out of 5 average rating, 197 reviews
Guest favorite
Guesthouse in Annapolis
Annapolis Guesthouse - Completely Separate Space
2 beds
Apr 21 – 26
4.91 out of 5 average rating, 174 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
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
Guest favorite
Cottage in Annapolis
Wright’s Cottage, Pets Welcome!
1 queen bed
Apr 21 – 26
4.94 out of 5 average rating, 312 reviews
Home in Annapolis
Quaint in the Heart of Annapolis
Apr 28 – May 3
New place to stay
Guest favorite
Guesthouse in Annapolis
Coastal Waterfront 1 Bedroom Cottage
Apr 21 – 26
4.99 out of 5 average rating, 104 reviews
Guest favorite
Townhouse in Annapolis
Historic 3 Bedroom Downtown Annapolis Townhome
5 beds
Apr 21 – 26
4.97 out of 5 average rating, 99 reviews
Superhost
Home in Annapolis
Historic Luxury Steps to USNA + Vibrant Waterfront
6 beds
Apr 21 – 26
New place to stay
Home in Annapolis
Vintage Charm: Annapolis Retreat
3 beds
May 5 – 10
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
Superhost
Home in Annapolis
Downtown Pinkney House w/Parking
2 queen beds
Apr 18 – 23
New place to stay