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Search results; Over 1,000 homes in Annapolis

Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
27 Jul – 1 Aug
4.89 out of 5 average rating, 358 reviews
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds
9–14 Nov
4.97 out of 5 average rating, 454 reviews
Top guest favourite
Flat in Annapolis
Perfect Eastport location
2 bedrooms, 3 beds
5–10 Jul
4.98 out of 5 average rating, 142 reviews
Top guest favourite
Home in Annapolis
Downtown Home/ Central Location
2 bedrooms, 6 beds
5–10 Jul
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
2 bedrooms, 4 beds
1–6 Jul
4.96 out of 5 average rating, 255 reviews
Top guest favourite
Home in Annapolis
Historic + Modern Home | Just Steps to Waterfront
2 bedrooms, 4 beds
13–18 Jul
5.0 out of 5 average rating, 47 reviews
Guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds
25–30 Oct
4.96 out of 5 average rating, 240 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
24–29 Jul
4.93 out of 5 average rating, 179 reviews
Guest favourite
Flat in Annapolis
King George Downtown Annapolis Getaway
2 bedrooms, 2 beds
5–10 Jul
4.86 out of 5 average rating, 122 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
9–14 Jul
4.93 out of 5 average rating, 179 reviews
Top guest favourite
Apartment in Annapolis
Cozy Annapolis Condo
2 bedrooms, 3 beds
28 Jul – 2 Aug
4.97 out of 5 average rating, 72 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
16–21 Jul
4.92 out of 5 average rating, 72 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed
26–31 Jul
4.95 out of 5 average rating, 180 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
13–18 Jul
4.98 out of 5 average rating, 57 reviews
Guest favourite
Home in Annapolis
Marymont Cottage
3 bedrooms, 3 beds
6–11 Jul
5.0 out of 5 average rating, 28 reviews
Guest favourite
Flat in Annapolis
Annapolis 4 Steps to Harbor Backs to Gate 1
1 bedroom, 2 beds
5–10 Jul
4.96 out of 5 average rating, 27 reviews
Guest favourite
Home in Annapolis
Cozy Cottage
2 bedrooms, 3 beds
5–10 Jul
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds
30 Jul – 4 Aug
4.96 out of 5 average rating, 110 reviews