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Search results; Over 1,000 homes in Annapolis

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Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
Studio, 2 beds, 1 private bathroom
18–23 Oct
,
4.96 out of 5 average rating, 179 reviews
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Top guest favourite
Home in Annapolis
Annapolis Charm –Bright 3BR in Downtown
3 bedrooms, 6 beds
27 Sept – 2 Oct
4.93 out of 5 average rating, 137 reviews
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Home in Annapolis
West street historic home
5 bedrooms, 6 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 74 reviews
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Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds
27 Sept – 2 Oct
4.91 out of 5 average rating, 92 reviews
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Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds
4–9 Dec
4.96 out of 5 average rating, 267 reviews
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Top guest favourite
Home in Annapolis
4 bedrooms, 7 beds, 3 bath completely updated
4 bedrooms, 7 beds
11–16 Oct
4.97 out of 5 average rating, 146 reviews
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Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
3–8 Oct
4.97 out of 5 average rating, 472 reviews
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Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 52 reviews
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Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds
30 Sept – 5 Oct
New place to stay
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Top guest favourite
Home in Annapolis
Charming on Charles Street
3 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 34 reviews
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Top guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds
20–25 Sept
5.0 out of 5 average rating, 147 reviews
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Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms
25–30 Oct
4.94 out of 5 average rating, 35 reviews
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Guest suite in Annapolis
Annapolis Home 5 miles from Downtown Annapolis
4 bedrooms, 4 beds
30 Sept – 5 Oct
New place to stay
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Top guest favourite
Guest suite in Annapolis
Cozy Naptown Perch
2 bedrooms, 3 beds
29 Oct – 3 Nov
4.96 out of 5 average rating, 228 reviews
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Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4 bedrooms, 6 beds
8–13 Nov
4.96 out of 5 average rating, 48 reviews
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Home in Annapolis
Beautiful 6BR home in Annapolis
6 bedrooms, 6 beds
4–9 Oct
4.64 out of 5 average rating, 70 reviews
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Top guest favourite
Home in Annapolis
Eastport Oasis
5 bedrooms, 5 beds
1–6 Nov
4.97 out of 5 average rating, 64 reviews
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Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds
26 Sept – 1 Oct
4.98 out of 5 average rating, 45 reviews
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Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds
8–13 Nov
5.0 out of 5 average rating, 23 reviews