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Search results; Over 1,000 homes in Annapolis

Guest favourite
Flat in Annapolis
Crow’s Nest Cottage - Down Under: Chesapeake Bay
3 bedrooms, 7 beds, 1 private bathroom
10–15 Sept
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4.96 out of 5 average rating, 23 reviews
Superhost
Home in Annapolis
Luxury Eastport Home w/ Chef’s Kitchen, Sleeps 16
3 bedrooms, 12 beds, 4.5 bathrooms
20–25 Sept
4.89 out of 5 average rating, 55 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds, 3.5 bathrooms
20–25 Sept
4.91 out of 5 average rating, 92 reviews
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 67 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
3–8 Oct
4.97 out of 5 average rating, 471 reviews
Guest favourite
Home in Annapolis
Stay Retro Naptown
4 bedrooms, 4 queen beds, 2 bathrooms
9–14 Nov
4.94 out of 5 average rating, 86 reviews
Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds, 1.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 bathroom
1–6 Jan
4.96 out of 5 average rating, 263 reviews
Guest favourite
Home in Annapolis
Cute bungalow blocks to Stadium
2 bedrooms, 3 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 81 reviews
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
2 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
4.87 out of 5 average rating, 77 reviews
Top guest favourite
Home in Annapolis
West street historic home
5 bedrooms, 6 beds, 3 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 73 reviews
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, 22 reviews
Top guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 147 reviews
Guest favourite
Home in Annapolis
West Annapolis Cottage- 6BR Walk to Navy Stadium
6 bedrooms, 10 beds, 5 bathrooms
10–15 Sept
4.97 out of 5 average rating, 90 reviews
Top guest favourite
Home in Edgewater
3 BRs House+Patio+Playground
3 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
4.93 out of 5 average rating, 105 reviews
Superhost
Townhouse in Annapolis
Annapolis Downtown Pleasant St Townhome 3 bedrooms
3 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
4.89 out of 5 average rating, 199 reviews
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 174 reviews
Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
3 bedrooms, 5 beds, 2 bathrooms
11–16 Sept
4.99 out of 5 average rating, 69 reviews
Top guest favourite
Home in Annapolis
3BR/2BA Annapolis Cottage
3 bedrooms, 4 beds, 2 bathrooms
10–15 Sept
4.98 out of 5 average rating, 227 reviews