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Search results; Over 1,000 homes in Annapolis

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Guest favourite
Apartment in Annapolis
Annapolis @Gate 1 steps to the Harbor Free parking
1 bedroom, 2 beds, 1 private bathroom
6–11 Sept
,
4.91 out of 5 average rating, 150 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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Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
13–18 Sept
4.93 out of 5 average rating, 192 reviews
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Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds
20–25 Sept
4.96 out of 5 average rating, 172 reviews
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Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed
20–25 Sept
4.95 out of 5 average rating, 189 reviews
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Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed
20–25 Sept
4.91 out of 5 average rating, 118 reviews
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Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds
3–8 Oct
4.92 out of 5 average rating, 61 reviews
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Guest favourite
Flat in Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
1 bedroom, 3 beds
12–17 Sept
4.92 out of 5 average rating, 523 reviews
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Superhost
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
13–18 Sept
4.94 out of 5 average rating, 189 reviews
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Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds
26–31 Oct
4.96 out of 5 average rating, 114 reviews
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Top guest favourite
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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Top guest favourite
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 favourite
Flat in Annapolis
The USNA Getaway!
1 bedroom, 3 beds
7–12 Sept
4.9 out of 5 average rating, 77 reviews
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Top guest favourite
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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Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
10–15 Sept
4.97 out of 5 average rating, 65 reviews
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Top guest favourite
Apartment in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
1 bedroom, 2 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 345 reviews
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Superhost
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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Top guest favourite
Home in Annapolis
Historic Home w/ Parking Steps From Capital & USNA
1 bedroom, 2 beds
10–15 Nov
4.98 out of 5 average rating, 104 reviews
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Top guest favourite
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
2 bedrooms, 2 beds
13–18 Sept
4.94 out of 5 average rating, 423 reviews