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Search results; Over 1,000 homes in Annapolis

Guest favorite
Apartment in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 bed, 1 bath
Aug 23 – 28
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4.89 out of 5 average rating, 368 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
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds, 2 baths
Aug 15 – 20
4.96 out of 5 average rating, 78 reviews
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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
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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
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Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed, 1 bath
Aug 29 – Sep 3
4.98 out of 5 average rating, 163 reviews
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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
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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
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Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
2 bedrooms, 6 beds, 2 baths
Aug 16 – 21
4.92 out of 5 average rating, 25 reviews
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Apartment in Annapolis
The Sail Loft
3 bedrooms, 4 beds, 2 baths
Aug 14 – 19
5.0 out of 5 average rating, 41 reviews
Guest favorite
Home in Annapolis
Annapolis Small House in Historic District.
1 bedroom, 2 beds, 1.5 baths
Aug 12 – 17
4.95 out of 5 average rating, 78 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
Guest favorite
Guesthouse in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 bedroom, 1 queen bed, 1 bath
Aug 12 – 17
4.95 out of 5 average rating, 210 reviews
Home in Annapolis
City Gate Sanctuary
4 bedrooms, 4 beds, 3.5 baths
Aug 16 – 21
New place to stay
Top guest favorite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds, 2 baths
Aug 18 – 23
4.96 out of 5 average rating, 114 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
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Guesthouse in Stevensville
Waterfront-View of Bay from your Bed
1 queen bed, 1 bath
Aug 16 – 21
4.99 out of 5 average rating, 359 reviews
Top guest favorite
Cottage in Annapolis
Secluded Cottage_ A+ Amenities in Historic Dwntwn
2 bedrooms, 3 queen beds, 1 bath
Aug 12 – 17
4.93 out of 5 average rating, 227 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