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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Guest suite in Annapolis
Cozy Naptown Perch
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
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4.96 out of 5 average rating, 224 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 74 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
27 Jul – 1 Aug
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
4.97 out of 5 average rating, 462 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
Top guest favourite
Home in Annapolis
CJ's Cottage
4.96 out of 5 average rating, 72 reviews, 2 bedrooms, 3 beds, 2 bathrooms
11–16 Jul
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment
4.9 out of 5 average rating, 104 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Home in Annapolis
Marymont Cottage
5.0 out of 5 average rating, 28 reviews, 3 bedrooms, 3 beds, 2 bathrooms
30 Jul – 4 Aug
Top guest favourite
Guest house in Annapolis
Private Art-Filled Guesthouse near Naval Academy
5.0 out of 5 average rating, 171 reviews, 1 bed, 1 bathroom
8–13 Jul
Top guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
5.0 out of 5 average rating, 21 reviews, 4 bedrooms, 6 beds, 2.5 bathrooms
23–28 Jul
Top guest favourite
Home in Annapolis
Quaint in the Heart of Annapolis
5.0 out of 5 average rating, 113 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Jul
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
4.95 out of 5 average rating, 221 reviews, 1 bedroom, 1 bed, 1 bathroom
8–13 Jul
Guest favourite
Home in Annapolis
1 Block to USNA Stadium: Modern Annapolis Home!
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Guest favourite
Flat in Annapolis
NEW lovely studio apartment with onsite parking!
4.85 out of 5 average rating, 124 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Flat in Annapolis
Annapolis Main Street Modern Apartment
5.0 out of 5 average rating, 47 reviews, 2 bedrooms, 2 beds, 1 bathroom
10–15 Jul
Top guest favourite
Guest house in Annapolis
Guesthouse on The Weems Creek
5.0 out of 5 average rating, 44 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Guest favourite
Home in Arnold
Rachel's BnB
4.9 out of 5 average rating, 135 reviews, 2 bedrooms, 3 beds, 1 bathroom
26–31 Jul
Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
4.95 out of 5 average rating, 134 reviews, 2 bedrooms, 3 beds, 1 bathroom
9–15 Sept
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
5.0 out of 5 average rating, 13 reviews, 4 bedrooms, 6 beds, 3 bathrooms
12–17 Sept
Guest favourite
Apartment in Annapolis
Semper Fi Condo
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul