filters

Search results; Over 1,000 homes in Annapolis

Photo 1 of 29
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 beds, 1 private bathroom
3–8 Oct
,
4.97 out of 5 average rating, 472 reviews
Photo 1 of 19
Featured hotel
Hotel in Annapolis
Historic Inns of Annapolis, Maryland Inn 2 double.
1 bedroom, 1 double bed
22–27 Nov
Photo 1 of 28
Guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds
1–6 Oct
4.94 out of 5 average rating, 16 reviews
Photo 1 of 26
Home in Annapolis
The 1845 Outpost
3 bedrooms, 3 king beds
1–6 Oct
New place to stay
Photo 1 of 12
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds
28 Dec – 2 Jan
4.97 out of 5 average rating, 464 reviews
Photo 1 of 10
Top guest favourite
Guest suite in Annapolis
Cozy Naptown Perch
2 bedrooms, 3 beds
29 Oct – 3 Nov
4.96 out of 5 average rating, 228 reviews
Photo 1 of 29
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed
17–22 Oct
5.0 out of 5 average rating, 226 reviews
Photo 1 of 29
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms, 6 beds
1–6 Oct
4.94 out of 5 average rating, 33 reviews
Photo 1 of 24
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
Photo 1 of 6
Top guest favourite
Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
2 bedrooms, 4 beds
31 Oct – 5 Nov
4.97 out of 5 average rating, 260 reviews
Photo 1 of 12
Flat in Annapolis
Annapolis Getaway | 2BR Sleeps 6 | Near USNA
3 bedrooms, 2 beds
1–6 Oct
New place to stay
Photo 1 of 15
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms
25–30 Oct
4.94 out of 5 average rating, 35 reviews
Photo 1 of 29
Home in Annapolis
Beautiful 6BR home in Annapolis
6 bedrooms, 6 beds
4–9 Oct
4.63 out of 5 average rating, 71 reviews
Photo 1 of 19
Top guest favourite
Home in Annapolis
Quiet Waterfront
3 bedrooms, 3 beds
6–11 Dec
4.98 out of 5 average rating, 191 reviews
Photo 1 of 23
Guest favourite
Home in Annapolis
Fleet St Retreat in Downtown - Great Location!
2 bedrooms, 3 beds
1–6 Nov
4.91 out of 5 average rating, 125 reviews
Photo 1 of 29
Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds
1–6 Oct
New place to stay
Photo 1 of 9
Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds
4–9 Dec
4.96 out of 5 average rating, 268 reviews
Photo 1 of 29
Guest favourite
Home in Annapolis
Beautiful house in the best location!
3 bedrooms, 6 beds
1–6 Oct
4.95 out of 5 average rating, 55 reviews
Photo 1 of 20
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
2 bedrooms, 4 beds
1–6 Oct
4.81 out of 5 average rating, 79 reviews