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Search results; Over 1,000 homes in Annapolis

Guest favourite
Apartment in Annapolis
Capts Qrtrs - Awesome downtown Annapolis location!
1 bedroom, 1 bed, 1 private bathroom
9–14 Aug
,
4.86 out of 5 average rating, 182 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
Weems Creek Cottage, Annapolis Waterfront
4.99 out of 5 average rating, 157 reviews, 1 bed, 1 bathroom
26–31 Jul
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
Charming Annapolis Townhome
4.98 out of 5 average rating, 58 reviews, 2 bedrooms, 1.5 bathrooms
19–24 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
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
Guest suite in Arnold
Coastal Comfort Retreat near Annapolis, EV charger
4.94 out of 5 average rating, 215 reviews, 1 bedroom, 2 beds, 1 bathroom
12–17 Jul
Top guest favourite
Home in Annapolis
Nautical Retreat 6 Guests • 3 BDR • 2 Baths
4.99 out of 5 average rating, 145 reviews, 3 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
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
CJ's Cottage
4.96 out of 5 average rating, 72 reviews, 2 bedrooms, 3 beds, 2 bathrooms
11–16 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
10–15 Jul
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
4.93 out of 5 average rating, 28 reviews, 3 bedrooms, 2 bathrooms
12–17 Jul
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
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
13–18 Jul
Hotel room in Annapolis
Governor Calvert King | Historic Inns
4.56 out of 5 average rating, 32 reviews, 1 bedroom, 1 bathroom
10–15 Jul
Top guest favourite
Home in Annapolis
Cozy 3BR Annapolis, Private Deck, Parking
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26–31 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