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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Guest suite in Annapolis
Pristine, Private Apt - Walk to Town/Stadium
1 bedroom, 2 beds, 1 private bathroom
29 Sept – 4 Oct
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5.0 out of 5 average rating, 54 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, 186 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
16–21 Aug
4.93 out of 5 average rating, 190 reviews
Room in Bowie
Cozy Private Queen Room | Free Parking | Near DC
1 queen bed, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 4 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, 187 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 bathroom
21–26 Aug
4.92 out of 5 average rating, 1132 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds, WC
17–22 Aug
4.93 out of 5 average rating, 60 reviews
Top guest favourite
Room in Annapolis
“Room at the Inn…”
1 queen bed, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Room in Stevensville
Rustic & Elegant Private Bed & Bath
1 bed, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 305 reviews
Guest favourite
Rooms in Edgewater
Cheerful 2 bedroom shared home with water views
2 bedrooms, 2 queen beds, 1 bathroom
15–20 Aug
4.86 out of 5 average rating, 92 reviews
Top guest favourite
Guest suite in Arnold
Coastal Comfort Retreat near Annapolis, EV charger
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.94 out of 5 average rating, 220 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 469 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
23–28 Aug
4.93 out of 5 average rating, 85 reviews
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
1 queen bed, 1 bathroom
24–29 Aug
4.96 out of 5 average rating, 423 reviews
Guest favourite
Rooms in Arnold
Annapolis Room - 3 miles from Naval Academy
2 bedrooms, 3 beds, 1 bathroom
13–18 Aug
4.86 out of 5 average rating, 102 reviews
Superhost
Guest suite in Millersville
The Lower Level Loft near BWI
1 bedroom, 2 queen beds, 1 bathroom
21–26 Aug
4.82 out of 5 average rating, 200 reviews
Top guest favourite
Place to stay in Annapolis
Guest Suite Getaway near Naval Academy Stadium
1 bed, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 173 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds, 1 bathroom
29 Oct – 3 Nov
5.0 out of 5 average rating, 32 reviews
Guest favourite
Guest house in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 bedroom, 1 queen bed, 1 bathroom
14–19 Aug
4.95 out of 5 average rating, 210 reviews