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Search results; Over 1,000 homes in Annapolis

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Top guest favourite
Cottage in Annapolis
Charming Waterfront Cottage on Historic Property
2 bedrooms, 3 beds, 1.5 private bathrooms
25–30 Oct
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4.95 out of 5 average rating, 66 reviews
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Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds
18–23 Oct
4.96 out of 5 average rating, 179 reviews
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Superhost
Flat in Annapolis
Charming Eastport
1 bedroom, 1 queen bed
20–25 Sept
4.77 out of 5 average rating, 303 reviews
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Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds
21–26 Sept
New place to stay
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Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
8–13 Nov
4.94 out of 5 average rating, 191 reviews
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Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds
4–9 Dec
4.96 out of 5 average rating, 266 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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Top guest favourite
Home in Annapolis
Historic Home w/ Parking Steps From Capital & USNA
1 bedroom, 2 beds
25–30 Oct
4.98 out of 5 average rating, 105 reviews
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Home in Cape St. Claire
Cutie in Annapolis near navy academy
4 bedrooms, 8 beds
21–26 Sept
New place to stay
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Top guest favourite
Cottage in Annapolis
Miller Cottage - near Navy Stadium
1 bedroom, 2 beds
2–7 Oct
4.99 out of 5 average rating, 162 reviews
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Flat in Annapolis
Annapolis Getaway | 2BR Sleeps 6 | Near USNA
3 bedrooms, 2 beds
20–25 Sept
New place to stay
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Guest favourite
Home in Annapolis
Beautiful house in the best location!
3 bedrooms, 6 beds
21–26 Sept
4.95 out of 5 average rating, 55 reviews
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Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
4–9 Oct
4.89 out of 5 average rating, 373 reviews
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Guest favourite
Flat in Annapolis
Charming Navy-Themed Townhome | Walk to USNA & DTA
2 bedrooms, 3 beds
28 Sept – 3 Oct
4.93 out of 5 average rating, 118 reviews
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Top guest favourite
Home in Annapolis
Historic & sunny home steps from USNA/downtown
3 bedrooms, 5 beds
29 Nov – 4 Dec
5.0 out of 5 average rating, 204 reviews
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Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds
4–9 Oct
4.97 out of 5 average rating, 99 reviews
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Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed
25–30 Oct
4.95 out of 5 average rating, 194 reviews
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Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
20–25 Sept
4.97 out of 5 average rating, 68 reviews
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Guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds
20–25 Sept
4.94 out of 5 average rating, 16 reviews