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Search results; Over 1,000 homes in Annapolis

Top guest favorite
Guest suite in Annapolis
Cozy Naptown Perch
2 bedrooms, 3 beds, 1 bath
Oct 18 – 23
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4.96 out of 5 average rating, 225 reviews
Guest favorite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 baths
Sep 20 – 25
4.95 out of 5 average rating, 186 reviews
Top guest favorite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 bath
Nov 1 – 6
4.92 out of 5 average rating, 1132 reviews
Top guest favorite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bath
Aug 30 – Sep 4
4.97 out of 5 average rating, 469 reviews
Guest favorite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds, Half-bath
Aug 17 – 22
4.93 out of 5 average rating, 60 reviews
Top guest favorite
Apartment in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 baths
Aug 23 – 28
4.93 out of 5 average rating, 85 reviews
Guest favorite
Home in Riva
Waterfront Annapolis Getaway!
1 bedroom, 1 king bed, 2.5 baths
Sep 7 – 12
4.92 out of 5 average rating, 95 reviews
Hotel room in Annapolis
Governor Calvert King | Historic Inns
1 bedroom, 1 king bed, 1 bath
Aug 19 – 24
4.62 out of 5 average rating, 37 reviews
Guest favorite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed, 1 bath
Aug 16 – 21
4.96 out of 5 average rating, 134 reviews
Top guest favorite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 baths
Aug 15 – 20
5.0 out of 5 average rating, 18 reviews
Guest favorite
Guesthouse in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 bedroom, 1 queen bed, 1 bath
Aug 13 – 18
4.95 out of 5 average rating, 210 reviews
Guest favorite
Home in Annapolis
Annapolis Small House in Historic District.
1 bedroom, 2 beds, 1.5 baths
Aug 13 – 18
4.95 out of 5 average rating, 78 reviews
Guest favorite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4 bedrooms, 6 beds, 3.5 baths
Aug 23 – 28
4.95 out of 5 average rating, 44 reviews
Guest favorite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
2 bedrooms, 6 beds, 2 baths
Aug 16 – 21
4.88 out of 5 average rating, 26 reviews
Top guest favorite
Guesthouse in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed, 1 bath
Oct 17 – 22
5.0 out of 5 average rating, 222 reviews
Top guest favorite
Apartment in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed, 1 bath
Aug 30 – Sep 4
4.91 out of 5 average rating, 114 reviews
Top guest favorite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds, 1 bath
Aug 16 – 21
4.97 out of 5 average rating, 97 reviews
Superhost
Guesthouse in Galesville
Nautical Charm and Relaxing Waterview!
1 queen bed, 1 bath
Aug 17 – 22
4.95 out of 5 average rating, 186 reviews
Top guest favorite
Condo in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bath
Aug 23 – 28
4.96 out of 5 average rating, 168 reviews