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Search results; Over 1,000 homes in Annapolis

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Guest favourite
Room in Annapolis
Cozy private room in Annapolis home
1 bedroom, 1 bed, 1 shared bathroom
28 Oct – 2 Nov
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4.84 out of 5 average rating, 480 reviews
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Guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed
1–6 Oct
4.95 out of 5 average rating, 139 reviews
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Top guest favourite
Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
2 bedrooms, 4 beds
31 Oct – 5 Nov
4.97 out of 5 average rating, 261 reviews
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Guest favourite
Home in Annapolis
Across from stadium - walk to downtown Annapolis!
4 bedrooms, 4 beds
4–9 Oct
4.9 out of 5 average rating, 136 reviews
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Top guest favourite
Room in Annapolis
Guest Suite Getaway near Naval Academy Stadium
1 bed
1–6 Oct
5.0 out of 5 average rating, 175 reviews
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Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
8–13 Nov
4.94 out of 5 average rating, 192 reviews
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Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed
4–9 Oct
4.91 out of 5 average rating, 53 reviews
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Top guest favourite
Home in Annapolis
4BR Walk to USNA & Dock · Parking
4 bedrooms, 4 beds
1–6 Oct
5.0 out of 5 average rating, 18 reviews
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Top guest favourite
Guest house in Annapolis
Guesthouse on The Weems Creek
1 bedroom, 1 queen bed
1–6 Oct
5.0 out of 5 average rating, 49 reviews
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Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
11–16 Oct
4.98 out of 5 average rating, 167 reviews
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Guest favourite
Flat in Annapolis
Charming Navy-Themed Townhome | Walk to USNA & DTA
2 bedrooms, 3 beds
1–6 Oct
4.93 out of 5 average rating, 118 reviews
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Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds
29 Nov – 4 Dec
5.0 out of 5 average rating, 21 reviews
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Top guest favourite
Home in Annapolis
Walk to Navy Stadium & Shops. No cleaning fee!
3 bedrooms, 4 beds
1–6 Oct
5.0 out of 5 average rating, 37 reviews
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Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed
1–6 Oct
4.96 out of 5 average rating, 230 reviews
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Guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 2 beds
25–30 Oct
4.92 out of 5 average rating, 97 reviews
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Flat in Annapolis
Annapolis Getaway | 2BR Sleeps 6 | Near USNA
3 bedrooms, 2 beds
4–9 Oct
New place to stay
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Guest favourite
Home in Annapolis
Annapolis Small House in Historic District.
1 bedroom, 2 beds
25–30 Oct
4.95 out of 5 average rating, 78 reviews
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Bed and breakfast in Annapolis
Stay right on Main Street Annapolis! Private room with double bed and bath.
1 bedroom, 1 bed
25–30 Oct
4.56 out of 5 average rating, 86 reviews
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Top guest favourite
Apartment in Annapolis
Funky Uptown Apt meets Downtown - Hist District
2 bedrooms, 2 beds
1–6 Oct
4.96 out of 5 average rating, 128 reviews