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Search results; Over 1,000 places in Annapolis

Home in Annapolis
Quaint in the Heart of Annapolis
2 queen beds
Apr 1 – 6
New place to stay
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
Room in Annapolis
Stay with JenniferHosting for 6 years,
Chesapeake Mornings
Apr 21 – 26
4.96 out of 5 average rating, 451 reviews
Guest favorite
Houseboat in Arnold
Boho Luxe Floating Tiny Home with 360 Views
1 queen bed
Apr 7 – 12
5.0 out of 5 average rating, 10 reviews
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
Coastal Waterfront 1 Bedroom Cottage
Apr 1 – 6
4.99 out of 5 average rating, 102 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
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
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
Guest suite in Arnold
Old Bay Bungalow
2 beds
Apr 6 – 11
4.96 out of 5 average rating, 560 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
Annapolis Waterfront Condo - Unit #: A-203
2 beds
Apr 10 – 15
4.96 out of 5 average rating, 208 reviews
Superhost
Home in Annapolis
Historic Luxury Steps to USNA + Vibrant Waterfront
6 beds
Apr 1 – 6
New place to stay
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
Home in Annapolis
New Hotel Chic
2 beds
May 5 – 10
4.95 out of 5 average rating, 340 reviews
Guest favorite
Home in Annapolis
Cozy 2br home w/ parking in downtown Annapolis
3 beds
Apr 1 – 6
4.94 out of 5 average rating, 284 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
Luxury Waterfront Annapolis/ Private Beach & Dock
3 king beds
Apr 1 – 6
5.0 out of 5 average rating, 103 reviews