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Search results; Over 1,000 homes in Annapolis

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Guest favourite
Home in Annapolis
Nautical Cottage in Annapolis
2 bedrooms, 2 beds, 1 bathroom
17–22 Sept
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4.86 out of 5 average rating, 21 reviews
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Guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
3 bedrooms, 4 beds
13–18 Sept
4.94 out of 5 average rating, 204 reviews
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Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 20 reviews
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Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds
26 Sept – 1 Oct
4.98 out of 5 average rating, 42 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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Flat in Annapolis
Beautiful Historic Home next to City Dock + USNA
3 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 62 reviews
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Home in Annapolis
The Red Door Cottage - Pet-Friendly!
2 bedrooms, 2 beds
29 Nov – 4 Dec
5.0 out of 5 average rating, 40 reviews
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Top guest favourite
Home in Annapolis
3BR/2BA Annapolis Cottage
3 bedrooms, 4 beds
7–12 Sept
4.98 out of 5 average rating, 226 reviews
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Top guest favourite
Home in Annapolis
Charming on Charles Street
3 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 33 reviews
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Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds
25–30 Oct
5.0 out of 5 average rating, 18 reviews
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Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
2 bedrooms, 4 beds
13–18 Sept
4.87 out of 5 average rating, 76 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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Townhouse in Annapolis
Moose’s Happy Place
3 bedrooms, 4 beds
25–30 Nov
5.0 out of 5 average rating, 113 reviews
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Home in Annapolis
Downtown Annapolis Home
4 bedrooms, 5 beds
9–14 Nov
4.99 out of 5 average rating, 100 reviews
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Home in Annapolis
Perfect Location! 200 steps to USNA & Downtown
2 bedrooms, 3 beds
6–11 Sept
5.0 out of 5 average rating, 45 reviews
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Flat in Annapolis
Elegant Uptown Condo w/Parking
2 bedrooms
20–25 Sept
4.97 out of 5 average rating, 62 reviews
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Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
3 bedrooms, 5 beds
7–12 Sept
4.99 out of 5 average rating, 69 reviews
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Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds
7–12 Sept
5.0 out of 5 average rating, 52 reviews
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Home in Edgewater
Waterfront getaway ready to relax with you
2 bedrooms, 1 queen bed
12–17 Sept
New place to stay