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Search results; Over 1,000 homes in Annapolis

Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 bed, 1 bathroom
4–9 Oct
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4.89 out of 5 average rating, 369 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
13–18 Sept
4.93 out of 5 average rating, 192 reviews
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
27 Sept – 2 Oct
4.96 out of 5 average rating, 172 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
4.91 out of 5 average rating, 116 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
20–25 Sept
4.95 out of 5 average rating, 187 reviews
Top guest favourite
Apartment in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 345 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
13–18 Sept
4.94 out of 5 average rating, 189 reviews
Top guest favourite
Place to stay in Annapolis
Guest Suite Getaway near Naval Academy Stadium
1 bed, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 173 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
4.92 out of 5 average rating, 1133 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.96 out of 5 average rating, 225 reviews
Top guest favourite
Guest house in Stevensville
Waterfront-View of Bay from your Bed
1 queen bed, 1 bathroom
21–26 Sept
4.99 out of 5 average rating, 361 reviews
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 1
1 king bed, 1 bathroom
7–12 Sept
4.94 out of 5 average rating, 359 reviews
Top guest favourite
Room in Annapolis
A Cottage Room in Presidents Hill
1 single bed, 1.5 bathrooms
12–17 Sept
4.88 out of 5 average rating, 181 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds, WC
1–6 Sept
4.92 out of 5 average rating, 61 reviews
Top guest favourite
Guest suite in Arnold
Old Bay Bungalow
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
4.96 out of 5 average rating, 760 reviews
Top guest favourite
Room in Annapolis
An Orange Room in Presidents Hill
1 double bed, 1.5 bathrooms
6–11 Sept
4.9 out of 5 average rating, 185 reviews
Top guest favourite
Cabin in Gambrills
Relaxing Cabin Get Away Near Annapolis & DC
1 bedroom, 3 beds, 1 bathroom
1–6 Sept
4.91 out of 5 average rating, 186 reviews
Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 114 reviews
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed, 1 bathroom
17–22 Oct
5.0 out of 5 average rating, 225 reviews