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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
Studio, 1 bed, 1 private bathroom
26–31 Jul
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4.99 out of 5 average rating, 157 reviews
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
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
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
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
Charming Annapolis Townhome
4.98 out of 5 average rating, 58 reviews, 2 bedrooms, 1.5 bathrooms
19–24 Jul
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
4.95 out of 5 average rating, 222 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 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
Apartment in Annapolis
Semper Fi Condo
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
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
Top guest favourite
Guest house in Annapolis
Eastport Gem ~ Walk to Downtown Annapolis
5.0 out of 5 average rating, 92 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
12–17 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
Guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
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
Guest house in Annapolis
Private Art-Filled Guesthouse near Naval Academy
5.0 out of 5 average rating, 171 reviews, 1 bed, 1 bathroom
9–14 Jul
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
4.97 out of 5 average rating, 93 reviews, 2 beds, 1 bathroom
16–21 Aug
Superhost
Home in Annapolis
Tide & Tallow - Walk to Downtown, Main St, Academy
4.74 out of 5 average rating, 35 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
12–17 Jul
Guest favourite
Flat in Annapolis
NEW lovely studio apartment with onsite parking!
4.85 out of 5 average rating, 125 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
5.0 out of 5 average rating, 14 reviews, 4 bedrooms, 6 beds, 3 bathrooms
12–17 Sept