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Search results; Over 1,000 homes in Annapolis

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Top guest favourite
Home in Annapolis
Modern Annapolis Getaway - 2 Free Parking Spaces
2 bedrooms, 2 beds, 1 private bathroom
27 Sept – 2 Oct
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5.0 out of 5 average rating, 119 reviews
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Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
20–25 Sept
4.93 out of 5 average rating, 192 reviews
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Guest suite in Annapolis
Bay View Studio Apartment
2 beds
4–9 Oct
4.97 out of 5 average rating, 98 reviews
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Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 172 reviews
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Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed
20–25 Sept
4.95 out of 5 average rating, 190 reviews
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Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds
20–25 Sept
4.91 out of 5 average rating, 92 reviews
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Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed
25–30 Oct
4.91 out of 5 average rating, 119 reviews
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Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed
17–22 Oct
5.0 out of 5 average rating, 225 reviews
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Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
20–25 Sept
4.97 out of 5 average rating, 66 reviews
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Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds
11–16 Sept
5.0 out of 5 average rating, 145 reviews
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Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds
3–8 Dec
4.97 out of 5 average rating, 460 reviews
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Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
3–8 Oct
4.97 out of 5 average rating, 470 reviews
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Flat in Annapolis
The USNA Getaway!
1 bedroom, 3 beds
7–12 Sept
4.9 out of 5 average rating, 78 reviews
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Townhouse in Annapolis
Annapolis Downtown Pleasant St Townhome 3 bedrooms
3 bedrooms, 3 beds
6–11 Sept
4.91 out of 5 average rating, 196 reviews
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Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds
3–8 Oct
4.87 out of 5 average rating, 62 reviews
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Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds
1–6 Nov
4.92 out of 5 average rating, 1135 reviews
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Room in Annapolis
Cozy private room in Annapolis home
1 bed
6–11 Sept
4.84 out of 5 average rating, 479 reviews
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Bungalow in Annapolis
Light, Bright and Comfortable! No cleaning fee!
3 bedrooms, 3 queen beds
21–26 Sept
4.89 out of 5 average rating, 84 reviews
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Room in Annapolis
“Room at the Inn…”
1 queen bed
27 Sept – 2 Oct
5.0 out of 5 average rating, 33 reviews