filters

Search results; Over 1,000 homes in Annapolis

Hotel room in Annapolis
Robert Johnson Suite at Historic Inns of Annapolis
1 bedroom, 1 bed, 1 private bathroom
20–25 Sept
,
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
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
20–25 Sept
4.97 out of 5 average rating, 68 reviews
Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Home in Annapolis
Annapolis Charm –Bright 3BR in Downtown
3 bedrooms, 6 beds
20–25 Sept
4.93 out of 5 average rating, 137 reviews
Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds
21–26 Sept
New place to stay
Top guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds
20–25 Sept
5.0 out of 5 average rating, 147 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Flat in Annapolis
Elegant Uptown Condo w/Parking
2 bedrooms
20–25 Sept
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Home in Annapolis
The Red Door Cottage - Pet-Friendly!
2 bedrooms, 2 beds
29 Nov – 4 Dec
5.0 out of 5 average rating, 43 reviews
Guest favourite
Home in Annapolis
Across from stadium - walk to downtown Annapolis!
4 bedrooms, 4 beds
4–9 Oct
4.9 out of 5 average rating, 136 reviews
Top guest favourite
Home in Annapolis
Historic + Modern Home | Just Steps to Waterfront
2 bedrooms, 4 beds
20–25 Sept
4.98 out of 5 average rating, 54 reviews
Top guest favourite
Home in Annapolis
Eastport Oasis
5 bedrooms, 5 beds
1–6 Nov
4.97 out of 5 average rating, 64 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, 34 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, 463 reviews
Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds
26 Sept – 1 Oct
4.98 out of 5 average rating, 44 reviews
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
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds
25–30 Oct
5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms, 6 beds
20–25 Sept
4.94 out of 5 average rating, 33 reviews