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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Annapolis
4 bedrooms, 7 beds, 3 bath completely updated
4 bedrooms, 7 beds, 3 private bathrooms
31 Jul – 5 Aug
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4.97 out of 5 average rating, 138 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
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
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
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
Flat in Annapolis
Perfect Eastport location
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
Our Annapolis Penthouse
1 bedroom, 2 beds, 1 bathroom
29 Nov – 4 Dec
4.97 out of 5 average rating, 455 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
Top guest favourite
Guest suite in Annapolis
Cozy Naptown Perch
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.96 out of 5 average rating, 224 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
30 Jul – 4 Aug
4.92 out of 5 average rating, 77 reviews
Superhost
Flat in Annapolis
Gybeset Eastport Inn
3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.88 out of 5 average rating, 303 reviews
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
1 queen bed, 1 bathroom
17–22 Aug
4.96 out of 5 average rating, 416 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
27 Jul – 1 Aug
4.98 out of 5 average rating, 58 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
14–19 Aug
4.97 out of 5 average rating, 463 reviews
Top guest favourite
Home in Annapolis
Elegant & Authentic Annapolis
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
Top guest favourite
Home in Annapolis
Gorgeous Historic Downtown Annapolis House
5 bedrooms, 9 beds, 3.5 bathrooms
15–20 Jul
4.98 out of 5 average rating, 156 reviews
Top guest favourite
Guest house in Annapolis
"The Perch" - Hot Tub - Beach - Chesapeake Bay
1 bedroom, 1 queen bed, 1 bathroom
26–31 Jul
4.9 out of 5 average rating, 94 reviews
Top guest favourite
Apartment in Annapolis
Funky Uptown Apt meets Downtown - Hist District
1 bedroom, 1 double bed, 1 bathroom
27 Jul – 1 Aug
4.96 out of 5 average rating, 122 reviews