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Search results; Over 1,000 homes in Annapolis

Descriptions are based on details hosts provide
Top guest favourite
Guest house in Annapolis
Carriage House near Navy Stadium, parking, pets
2 bedrooms, 4 beds, 1 private bathroom
26–31 Jul
,
4.95 out of 5 average rating, 117 reviews
Top guest favourite
Cottage in Annapolis
Mill Creek views from a wooded porch
2 bedrooms, 2 king beds, 1 bathroom
14–19 Aug
4.97 out of 5 average rating, 463 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed, 1 bathroom
10–15 Aug
4.89 out of 5 average rating, 361 reviews
Guest favourite
Room in Annapolis
1926 Four Square home with fire pit
1 queen bed, 1.5 bathrooms
10–15 Aug
4.93 out of 5 average rating, 183 reviews
Superhost
Home in Annapolis
Harbor’s Edge Retreat: Walk to Main St & Academy
3 bedrooms, 3 beds, 1.5 bathrooms
19–24 Jul
4.89 out of 5 average rating, 81 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
1–6 Aug
4.93 out of 5 average rating, 179 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.92 out of 5 average rating, 1125 reviews
Top guest favourite
Flat in Annapolis
Nautical Eastport pad with private courtyard
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
4.98 out of 5 average rating, 144 reviews
Top guest favourite
Guest suite in Annapolis
Fire pit and patio near downtown
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.96 out of 5 average rating, 224 reviews
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds, 1 bathroom
29 Nov – 4 Dec
4.97 out of 5 average rating, 455 reviews
Guest favourite
Guest house in Annapolis
West Annapolis cottage with a fire pit
1 bedroom, 1 king bed, 1 bathroom
16–21 Aug
4.9 out of 5 average rating, 355 reviews
Top guest favourite
Room in Annapolis
Cape Cod home with pool and hot tub
1 queen bed, 1 bathroom
17–22 Aug
4.96 out of 5 average rating, 416 reviews
Top guest favourite
Flat in Annapolis
Screened porch one block from Main St
2 bedrooms, 1 queen bed, 1.5 bathrooms
30 Jul – 4 Aug
4.92 out of 5 average rating, 76 reviews
Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 bathroom
27 Nov – 2 Dec
4.96 out of 5 average rating, 245 reviews
Superhost
Flat in Annapolis
1930s craftsman in walkable Eastport
3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.88 out of 5 average rating, 303 reviews
Top guest favourite
Home in Annapolis
Renovated historic brick home, walk everywhere
5 bedrooms, 9 beds, 3.5 bathrooms
15–20 Jul
4.98 out of 5 average rating, 156 reviews
Top guest favourite
Home in Annapolis
Newly renovated, walkable to downtown Annapolis
2 bedrooms, 1.5 bathrooms
27 Jul – 1 Aug
4.98 out of 5 average rating, 58 reviews
Top guest favourite
Home in Annapolis
Historic home 2 blocks from the water
1 bedroom, 1 queen bed, 1 bathroom
19–24 Jul
4.99 out of 5 average rating, 151 reviews
Guest favourite
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
2 bedrooms, 2 beds, 1 bathroom
25–30 Jul
4.94 out of 5 average rating, 418 reviews