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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Cape St. Claire
Beach Access, Hot Tub, Pet Friendly, Fully Fenced
4 bedrooms, 4 beds, 2.5 private bathrooms
28 Sept – 3 Oct
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4.99 out of 5 average rating, 142 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
Home in Annapolis
The King's Court
4 bedrooms, 4 beds
10–15 Sept
5.0 out of 5 average rating, 26 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
Home in Annapolis
Charming on Charles Street
3 bedrooms, 4 beds
19–24 Sept
5.0 out of 5 average rating, 33 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
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
The Sail Loft
3 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 43 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
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
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
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
Guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed
7–12 Sept
4.95 out of 5 average rating, 137 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
Waterfront Oasis in Eastport-Easy Walk to Downtown
5 bedrooms, 8 beds
13–18 Sept
4.93 out of 5 average rating, 124 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
Townhouse in Annapolis
Beautiful Downtown Annapolis Townhome!
3 bedrooms, 7 beds
13–18 Sept
5.0 out of 5 average rating, 119 reviews
Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds
7–12 Sept
4.95 out of 5 average rating, 146 reviews