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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, 109 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
Guest favorite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 king beds
Apr 23 – 28
4.96 out of 5 average rating, 332 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
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, 102 reviews
Superhost
Condo in Annapolis
Charming Annapolis Waterfront Condo
3 beds
Apr 21 – 26
5.0 out of 5 average rating, 4 reviews
Guest favorite
Home in Annapolis
New Hotel Chic
2 beds
Jun 9 – 14
4.95 out of 5 average rating, 345 reviews
Guest favorite
Guesthouse in Glen Burnie
The Crab House - a Private, Waterfront Guest House
1 queen bed
Apr 30 – May 5
4.94 out of 5 average rating, 263 reviews
Guest favorite
Home in Annapolis
Nautical Luxe Retreat! 6 Guests • 3 BDR • 2 Baths
3 beds
May 6 – 11
5.0 out of 5 average rating, 24 reviews
Superhost
Cottage in Annapolis
Waterfront cottage w/hot tub/ gated/ pier/ firepit
5 beds
Apr 21 – 26
4.83 out of 5 average rating, 48 reviews
Guest favorite
Home in Annapolis
Charming Annapolis Retreat with Hidden Wine Room
3 beds
May 5 – 10
4.97 out of 5 average rating, 31 reviews
Guest favorite
Home in Annapolis
Chesapeake Comfort, Annapolis.
4 beds
May 5 – 10
4.97 out of 5 average rating, 132 reviews
Guest favorite
Condo in Annapolis
Brand New Reno in Historic Dist w 2 Parking spots
3 beds
Jul 14 – 19
4.94 out of 5 average rating, 345 reviews
Superhost
Home in Annapolis
Downtown Pinkney House w/Parking
2 queen beds
Apr 20 – 25
New place to stay
Guest favorite
Apartment in Annapolis
LOCATION!! Steps away from historic Main Street.
3 beds
Apr 29 – May 4
5.0 out of 5 average rating, 66 reviews
Guest favorite
Home in Annapolis
Charming Downtwn Home, Private Parking Patio&Yard!
5 beds
Apr 28 – May 3
4.99 out of 5 average rating, 82 reviews
Guest favorite
Guesthouse in Stevensville
Waterfront Getaway - View of bay from your bed
1 queen bed
Apr 24 – 29
5.0 out of 5 average rating, 206 reviews
Guest favorite
Home in Annapolis
NEW - Downtwn Townhouse w/Parking & Patio! Unit C.
3 beds
Apr 20 – 25
4.96 out of 5 average rating, 25 reviews