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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Guest suite in Annapolis
Independent Access Garage Apartment, Near Downtown
1 bedroom, 1 bed, 1 private bathroom
5–10 Jul
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4.89 out of 5 average rating, 428 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
4.89 out of 5 average rating, 358 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Jul – 1 Aug
Top guest favourite
Flat in Annapolis
Perfect Eastport location
4.98 out of 5 average rating, 142 reviews, 2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
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
9–14 Nov
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
4.93 out of 5 average rating, 179 reviews, 1 queen bed, 1.5 bathrooms
24–29 Jul
Top guest favourite
Home in Annapolis
Downtown Home/ Central Location
4.94 out of 5 average rating, 36 reviews, 2 bedrooms, 6 beds, 2 bathrooms
5–10 Jul
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
9–14 Jul
Top guest favourite
Guest suite in Annapolis
Restful guest suite, scent-free, step-free
5.0 out of 5 average rating, 36 reviews, 3 bedrooms, 3 beds, 1 bathroom
7–12 Jul
Top guest favourite
Home in Annapolis
Historic + Modern Home | Just Steps to Waterfront
5.0 out of 5 average rating, 47 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
13–18 Jul
Top guest favourite
Apartment in Annapolis
Cozy Annapolis Condo
4.97 out of 5 average rating, 72 reviews, 2 bedrooms, 3 beds, 1 bathroom
28 Jul – 2 Aug
Guest favourite
Home in Annapolis
Cozy Cottage
4.96 out of 5 average rating, 25 reviews, 2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
Guest favourite
Home in Annapolis
Marymont Cottage
5.0 out of 5 average rating, 28 reviews, 3 bedrooms, 3 beds, 2 bathrooms
6–11 Jul
Guest favourite
Home in Annapolis
Historic Downtown in-law suite
4.96 out of 5 average rating, 240 reviews, 1 bedroom, 2 beds, 1 bathroom
25–30 Oct
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 72 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
16–21 Jul
Guest favourite
Home in Annapolis
Charming Eastport Getaway – Near Downtown & USNA
4.89 out of 5 average rating, 101 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
5–10 Jul
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
4.98 out of 5 average rating, 57 reviews, 2 bedrooms, 1.5 bathrooms
13–18 Jul
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
4.99 out of 5 average rating, 154 reviews, 1 bed, 1 bathroom
6–11 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
5–10 Jul
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
4.95 out of 5 average rating, 180 reviews, 1 queen bed, 3 bathrooms
26–31 Jul