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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Apartment in Annapolis
New Downtown Annapolis Condo With Free Parking
2 bedrooms, 2 beds, 2 private bathrooms
3–10 Oct
,
4.98 out of 5 average rating, 165 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
4.97 out of 5 average rating, 463 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Aug
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
4.93 out of 5 average rating, 179 reviews, 1 queen bed, 1.5 bathrooms
1–6 Aug
Guest favourite
Home in Annapolis
Historic Downtown in-law suite
4.96 out of 5 average rating, 243 reviews, 1 bedroom, 2 beds, 1 bathroom
25–30 Oct
Top guest favourite
Apartment in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
4.96 out of 5 average rating, 341 reviews, 1 bedroom, 2 beds, 1 bathroom
24–29 Aug
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
4.89 out of 5 average rating, 361 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Top guest favourite
Flat in Annapolis
Perfect Eastport location
4.98 out of 5 average rating, 144 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Superhost
Flat in Annapolis
Gybeset Eastport Inn
4.88 out of 5 average rating, 303 reviews, 3 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Top guest favourite
Boat in Annapolis
Welcome Aboard!
4.96 out of 5 average rating, 111 reviews, 2 bedrooms, 3 beds, 2 bathrooms
29 Jul – 3 Aug
Top guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
5.0 out of 5 average rating, 9 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
19–24 Jul
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
4.95 out of 5 average rating, 21 reviews, 2 bedrooms, 6 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
4.98 out of 5 average rating, 58 reviews, 2 bedrooms, 1.5 bathrooms
19–24 Jul
Top guest favourite
Home in Annapolis
Historic + Modern Home | Just Steps to Waterfront
5.0 out of 5 average rating, 49 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
13–18 Jul
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
4.93 out of 5 average rating, 180 reviews, 1 queen bed, 1.5 bathrooms
24–29 Jul
Top guest favourite
Home in Annapolis
Historic Charm | Steps from City Dock and the Yard
4.95 out of 5 average rating, 44 reviews, 2 bedrooms, 4 beds, 2.5 bathrooms
12–17 Jul
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
4.93 out of 5 average rating, 58 reviews, 1 bedroom, 2 beds, Toilet with sink
10–15 Jul
Guest favourite
Flat in Annapolis
King George Downtown Annapolis Getaway
4.86 out of 5 average rating, 122 reviews, 2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 76 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
30 Jul – 4 Aug
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
4.97 out of 5 average rating, 454 reviews, 1 bedroom, 2 beds, 1 bathroom
29 Nov – 4 Dec