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Search results; Over 1,000 homes in Annapolis

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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, 268 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, 179 reviews
Photo 1 of 19
Top guest favourite
Home in Annapolis
Quiet Waterfront
3 bedrooms, 3 beds, 3 bathrooms
6–11 Dec
4.98 out of 5 average rating, 190 reviews
Photo 1 of 29
Top guest favourite
Home in Annapolis
4BR Walk to USNA & Dock · Parking
4 bedrooms, 4 beds, 4 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 18 reviews
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Hotel room in Annapolis
Governor Calvert King | Historic Inns
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
4.57 out of 5 average rating, 44 reviews
Photo 1 of 9
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 229 reviews
Photo 1 of 29
Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4 bedrooms, 6 beds, 3.5 bathrooms
8–13 Nov
4.96 out of 5 average rating, 48 reviews
Photo 1 of 6
Guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 138 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
Photo 1 of 6
Guest favourite
Room in Annapolis
Laura’s Room
1 double bed, 1 bathroom
27 Sept – 2 Oct
4.88 out of 5 average rating, 95 reviews
Photo 1 of 29
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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Flat in Annapolis
Annapolis Getaway | 2BR Sleeps 6 | Near USNA
3 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
New place to stay
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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, 194 reviews
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Flat in Annapolis
Prime Eastport Location-10 Min Walk to City Dock
1 bedroom, 1 queen bed, 1 bathroom
11–16 Oct
New place to stay
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Top guest favourite
Flat in Annapolis
Well-appointed 1 bedroom, 1 bath in Annap/Eastport
1 bedroom, 2 beds, 1 bathroom
21–26 Sept
4.96 out of 5 average rating, 96 reviews
Photo 1 of 29
Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
30 Sept – 5 Oct
New place to stay
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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
Photo 1 of 29
Top guest favourite
Cottage in Annapolis
Charming Cottage 2 parking spot easy walk downtown
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.94 out of 5 average rating, 214 reviews