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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds, 2 private bathrooms
18–23 Aug
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4.96 out of 5 average rating, 111 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
4.93 out of 5 average rating, 181 reviews, 1 queen bed, 1.5 bathrooms
16–21 Aug
Top guest favourite
Room in Annapolis
Cozy Annapolis Retreat – Private Bedroom & Bath
5.0 out of 5 average rating, 37 reviews, 1 queen bed, 1 bathroom
26–31 Jul
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
4.97 out of 5 average rating, 463 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Aug
Top guest favourite
Room in Annapolis
Modern Suite with Spa Feel Near Downtown Annapolis
4.88 out of 5 average rating, 58 reviews, 1 king bed, 1 bathroom
26–31 Jul
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
4.93 out of 5 average rating, 186 reviews, 1 queen bed, 1.5 bathrooms
10–15 Aug
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
4.92 out of 5 average rating, 1126 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
4.97 out of 5 average rating, 455 reviews, 1 bedroom, 2 beds, 1 bathroom
29 Nov – 4 Dec
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
4.93 out of 5 average rating, 30 reviews, 3 bedrooms, 2 bathrooms
26–31 Jul
Guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
4.97 out of 5 average rating, 38 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
9–14 Aug
Top guest favourite
Home in Annapolis
Cute bungalow blocks to Stadium
4.96 out of 5 average rating, 72 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Jul
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
4.96 out of 5 average rating, 417 reviews, 1 queen bed, 1 bathroom
17–22 Aug
Guest favourite
Apartment in Annapolis
Semper Fi Condo
4.94 out of 5 average rating, 17 reviews, 2 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 78 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
23–28 Aug
Hotel room in Annapolis
Historic Inn Stay | Steps from Maryland State
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 1 bathroom
25–30 Jul
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
4.95 out of 5 average rating, 182 reviews, 1 queen bed, 3 bathrooms
26–31 Jul
Top guest favourite
Guest house in Annapolis
Guesthouse on The Weems Creek
5.0 out of 5 average rating, 45 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
4.9 out of 5 average rating, 355 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Top guest favourite
Room in Arnold
Beautiful bedroom, beautiful view near Annapolis
4.98 out of 5 average rating, 87 reviews, 1 double bed, 1.5 bathrooms
25–30 Jul