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Search results; Over 1,000 homes in Annapolis

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Top guest favourite
Cottage in Annapolis
Charming Cottage 2 parking spot easy walk downtown
2 bedrooms, 3 beds, 2 private bathrooms
1–6 Nov
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4.94 out of 5 average rating, 214 reviews
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Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
18–23 Oct
4.96 out of 5 average rating, 178 reviews
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Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 23 reviews
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Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4 bedrooms, 6 beds, 3.5 bathrooms
4–9 Oct
4.96 out of 5 average rating, 48 reviews
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Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
21–26 Sept
New place to stay
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Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 bathroom
4–9 Dec
4.96 out of 5 average rating, 266 reviews
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Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
4.89 out of 5 average rating, 373 reviews
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Top guest favourite
Cottage in Annapolis
Miller Cottage - near Navy Stadium
1 bedroom, 2 beds, 1 bathroom
2–7 Oct
4.99 out of 5 average rating, 162 reviews
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Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
25–30 Oct
4.95 out of 5 average rating, 193 reviews
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Guest favourite
Flat in Annapolis
Charming Navy-Themed Townhome | Walk to USNA & DTA
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
4.93 out of 5 average rating, 118 reviews
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Guest favourite
Guest suite in Arnold
Pet-Friendly King Suite + Kitchen | Near Annapolis
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 216 reviews
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Top guest favourite
Room in Annapolis
A Cottage Room in Presidents Hill
1 single bed, 1.5 bathrooms
20–25 Sept
4.89 out of 5 average rating, 185 reviews
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Top guest favourite
Home in Annapolis
Historic & sunny home steps from USNA/downtown
3 bedrooms, 5 beds, 2.5 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 204 reviews
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Guest favourite
Hotel room in Annapolis
Historic Inn Stay | Steps from Maryland State
1 bedroom, 1 double bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews
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Guest suite in Annapolis
Annapolis Home 5 miles from Downtown Annapolis
4 bedrooms, 4 beds, 4 bathrooms
16–21 Sept
New place to stay
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Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 99 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 bathroom
1–6 Nov
4.92 out of 5 average rating, 1139 reviews
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Guest favourite
Room in Annapolis
Cozy private room in Annapolis home
1 bed, 1 bathroom
28 Oct – 2 Nov
4.84 out of 5 average rating, 480 reviews
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Guest favourite
Home in Annapolis
Beautiful house in the best location!
3 bedrooms, 6 beds, 3.5 bathrooms
21–26 Sept
4.95 out of 5 average rating, 55 reviews