filters

Search results; Over 1,000 homes in Annapolis

Photo 1 of 29
Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4 bedrooms, 6 beds, 3.5 bathrooms
8–13 Nov
4.96 out of 5 average rating, 48 reviews
Photo 1 of 29
Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
30 Sept – 5 Oct
New place to stay
Photo 1 of 7
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
4.89 out of 5 average rating, 373 reviews
Photo 1 of 29
Top guest favourite
Home in Annapolis
4BR Walk to USNA & Dock · Parking
4 bedrooms, 4 beds, 4 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 18 reviews
Photo 1 of 29
Guest suite in Annapolis
Annapolis Home 5 miles from Downtown Annapolis
4 bedrooms, 4 beds, 4 bathrooms
19–24 Sept
New place to stay
Photo 1 of 29
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds, 2.5 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 20 reviews
Photo 1 of 6
Guest favourite
Room in Annapolis
Laura’s Room
1 double bed, 1 bathroom
20–25 Sept
4.88 out of 5 average rating, 95 reviews
Photo 1 of 24
Top guest favourite
Home in Annapolis
The Red Door Cottage - Pet-Friendly!
2 bedrooms, 2 beds, 2 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 43 reviews
Photo 1 of 23
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 83 reviews
Photo 1 of 22
Guest favourite
Guest suite in Arnold
Pet-Friendly King Suite + Kitchen | Near Annapolis
1 bedroom, 2 beds, 1 bathroom
21–26 Sept
4.95 out of 5 average rating, 216 reviews
Photo 1 of 14
Hotel room in Annapolis
Governor Calvert King | Historic Inns
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
4.57 out of 5 average rating, 44 reviews
Photo 1 of 29
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 68 reviews
Photo 1 of 19
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
18–23 Oct
4.96 out of 5 average rating, 179 reviews
Photo 1 of 28
Top guest favourite
Home in Annapolis
Modern Annapolis Getaway - 2 Free Parking Spaces
2 bedrooms, 2 double beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 122 reviews
Photo 1 of 29
Top guest favourite
Cottage in Annapolis
Charming City Retreat. Walk-harbor, eateries.USNA
4 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.87 out of 5 average rating, 118 reviews
Photo 1 of 14
Top guest favourite
Guest house in Annapolis
Guesthouse on The Weems Creek
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 49 reviews
Photo 1 of 18
Top guest favourite
Home in Annapolis
Historic Home w/ Parking Steps From Capital & USNA
1 bedroom, 2 beds, 1.5 bathrooms
25–30 Oct
4.98 out of 5 average rating, 105 reviews
Photo 1 of 26
Home in Annapolis
The 1845 Outpost
3 bedrooms, 3 king beds, 2 bathrooms
20–25 Sept
New place to stay