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Search results; Over 1,000 homes in Annapolis

Top guest favourite
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, 262 reviews
Top guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds
8–13 Sept
5.0 out of 5 average rating, 146 reviews
Guest favourite
Flat in Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
1 bedroom, 3 beds
12–17 Sept
4.92 out of 5 average rating, 524 reviews
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 174 reviews
Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds
7–12 Sept
5.0 out of 5 average rating, 52 reviews
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
Top guest favourite
Cottage in Annapolis
Charming City Oasis. Walk to harbor, eateries.USNA
4 bedrooms, 4 beds
8–13 Sept
4.87 out of 5 average rating, 117 reviews
Guest favourite
Flat in Annapolis
Uptown Condo w 2 Parking Spots
1 bedroom
13–18 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Annapolis
3BR/2BA Annapolis Cottage
3 bedrooms, 4 beds
7–12 Sept
4.98 out of 5 average rating, 226 reviews
Top guest favourite
Flat in Annapolis
Perfect Eastport location
2 bedrooms, 3 beds
8–13 Sept
4.98 out of 5 average rating, 147 reviews
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
20–25 Sept
4.97 out of 5 average rating, 66 reviews
Top guest favourite
Flat in Annapolis
The Sail Loft
3 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms
13–18 Sept
4.94 out of 5 average rating, 33 reviews
Top guest favourite
Cottage in Annapolis
Charming Cottage 2 parking spot easy walk downtown
2 bedrooms, 3 beds
1–6 Nov
4.94 out of 5 average rating, 214 reviews
Top guest favourite
Home in Annapolis
Nautical - and SO nice! Park Free Walk to Stadium
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Home in Annapolis
Southgate Sanctuary - Downtown Annapolis
3 bedrooms, 3 beds
14–19 Sept
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds
3–8 Dec
4.97 out of 5 average rating, 461 reviews
Top guest favourite
Home in Annapolis
Cozy 3BR Annapolis, Private Deck, Parking
3 bedrooms, 3 beds
21–26 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Home in Annapolis
Charming on Charles Street
3 bedrooms, 4 beds
19–24 Sept
5.0 out of 5 average rating, 33 reviews