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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Secluded Cottage_ A+ Amenities in Historic Dwntwn
2 bedrooms, 3 beds, 1 private bathroom
15–20 Jul
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4.93 out of 5 average rating, 223 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 75 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
27 Jul – 1 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, 462 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 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
Loft in Annapolis
Step Out to Main Street From a Chic Loft
4.92 out of 5 average rating, 1123 reviews, 1 bedroom, 2 beds, 1 bathroom
10–15 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
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
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
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
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 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
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
8–13 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
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 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
Guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 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
12–17 Jul