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Search results; Over 1,000 homes in Annapolis

Bed and breakfast in Annapolis
Stay right on Main Street Annapolis! Private room with double bed and bath.
1 bedroom, 1 bed, 1 bathroom
21–26 Jul
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4.55 out of 5 average rating, 83 reviews
Top guest favourite
Room in Annapolis
Cozy Annapolis Retreat – Private Bedroom & Bath
1 queen bed, 1 bathroom
26–31 Jul
5.0 out of 5 average rating, 37 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
16–21 Aug
4.93 out of 5 average rating, 181 reviews
Top guest favourite
Room in Annapolis
Modern Suite with Spa Feel Near Downtown Annapolis
1 king bed, 1 bathroom
26–31 Jul
4.88 out of 5 average rating, 58 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
10–15 Aug
4.93 out of 5 average rating, 186 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
14–19 Aug
4.97 out of 5 average rating, 463 reviews
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Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.92 out of 5 average rating, 1127 reviews
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Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds, 1 bathroom
29 Nov – 4 Dec
4.97 out of 5 average rating, 455 reviews
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Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
23–28 Aug
4.92 out of 5 average rating, 78 reviews
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
1 queen bed, 1 bathroom
17–22 Aug
4.96 out of 5 average rating, 417 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms, 2 bathrooms
26–31 Jul
4.93 out of 5 average rating, 30 reviews
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Home in Annapolis
Cute bungalow blocks to Stadium
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Jul
4.96 out of 5 average rating, 72 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
26–31 Jul
4.95 out of 5 average rating, 182 reviews
Guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed, 1 bathroom
21–26 Jul
4.96 out of 5 average rating, 131 reviews
Top guest favourite
Guest house in Annapolis
Guesthouse on The Weems Creek
1 bedroom, 1 queen bed, 1 bathroom
22–27 Jul
5.0 out of 5 average rating, 45 reviews
Superhost
Flat in Annapolis
Walk to Navy Stadium | Private Studio w/ Parking
1 bedroom, 1 queen bed, 1 bathroom
25–30 Jul
New place to stay
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Guest suite in Annapolis
Cozy Naptown Perch
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.96 out of 5 average rating, 224 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed, 1 bathroom
16–21 Aug
4.91 out of 5 average rating, 108 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed, 1 bathroom
21–26 Jul
4.96 out of 5 average rating, 224 reviews