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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Annapolis
Beach Access, Hot Tub, Pet Friendly, Fully Fenced
4 bedrooms, 4 beds, 2.5 private baths
Sep 13–18
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4.99 out of 5 average rating, 140 reviews
Top guest favourite
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 favourite
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 favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 baths
Sep 13–18
4.94 out of 5 average rating, 187 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds, 2 baths
Aug 15–20
4.96 out of 5 average rating, 78 reviews
Top guest favourite
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 favourite
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
Top guest favourite
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 favourite
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
Top guest favourite
Condo in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bath
Aug 23–28
4.96 out of 5 average rating, 168 reviews
Top guest favourite
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
Guest favourite
Apartment in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed, 1 bath
Aug 13–18
4.9 out of 5 average rating, 49 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed, 1 bath
Aug 13–18
4.96 out of 5 average rating, 225 reviews
Guest favourite
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
Guest favourite
Guesthouse in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 king bed, 1 bath
Sep 20–25
4.9 out of 5 average rating, 362 reviews
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
1 queen bed, 1 bath
Aug 24–29
4.96 out of 5 average rating, 423 reviews
Top guest favourite
Guesthouse in Annapolis
Guesthouse on The Weems Creek
1 bedroom, 1 queen bed, 1 bath
Aug 16–21
5.0 out of 5 average rating, 46 reviews
Hotel room in Annapolis
Governor Calvert King | Historic Inns
1 bedroom, 1 king bed, 1 bath
Aug 23–28
4.62 out of 5 average rating, 37 reviews
Guest favourite
Apartment in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed, 1 bath
Aug 23–28
4.89 out of 5 average rating, 368 reviews