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Search results; Over 1,000 homes in Annapolis

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Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 private bathroom
27 Nov – 2 Dec
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4.96 out of 5 average rating, 259 reviews
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Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds
7–12 Sept
4.93 out of 5 average rating, 14 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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Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed
25–30 Oct
4.91 out of 5 average rating, 118 reviews
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Home in Annapolis
Quiet Waterfront
3 bedrooms, 3 beds
6–11 Dec
4.98 out of 5 average rating, 189 reviews
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Home in Annapolis
4 bedrooms, 7 beds, 3 bath completely updated
4 bedrooms, 7 beds
19–24 Sept
4.97 out of 5 average rating, 145 reviews
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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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Guest favourite
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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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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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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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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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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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 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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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 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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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