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Search results; Over 1,000 homes in Annapolis

Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
16–21 Aug
4.93 out of 5 average rating, 180 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
30 Jul – 4 Aug
4.92 out of 5 average rating, 78 reviews
Home in Annapolis
Waterfront Gem w/ Dock: 2 Mi to Dwtn Annapolis!
4 bedrooms, 6 beds
1–6 Aug
New place to stay
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
10–15 Aug
4.93 out of 5 average rating, 183 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
14–19 Aug
4.97 out of 5 average rating, 463 reviews
Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds
21–26 Jul
4.96 out of 5 average rating, 111 reviews
Superhost
Flat in Annapolis
Modern Eastport Getaway, Near Historic Annapolis
1 bedroom, 3 beds
19–24 Jul
4.84 out of 5 average rating, 19 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed
26–31 Jul
4.95 out of 5 average rating, 182 reviews
Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4 bedrooms, 6 beds
23–28 Aug
4.98 out of 5 average rating, 40 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds
15–20 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds
16–21 Aug
4.97 out of 5 average rating, 93 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
26–31 Jul
4.98 out of 5 average rating, 160 reviews
Top guest favourite
Home in Annapolis
Stay Retro Naptown
4 bedrooms, 4 queen beds
24–29 Jul
4.95 out of 5 average rating, 80 reviews
Top guest favourite
Guest house in Annapolis
Private Art-Filled Guesthouse near Naval Academy
1 bed
17–22 Jul
5.0 out of 5 average rating, 171 reviews
Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds
9–15 Sept
4.95 out of 5 average rating, 137 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
10–15 Aug
4.89 out of 5 average rating, 362 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds
13–18 Aug
5.0 out of 5 average rating, 27 reviews
Hotel room in Annapolis
Historic Inn Stay | Steps from Maryland State
1 bedroom, 1 double bed
19–24 Jul
New place to stay