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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Annapolis
Beach Access, Hot Tub, Pet Friendly, Fully Fenced
4 bedrooms, 4 beds, 2.5 private bathrooms
13–18 Sept
,
4.99 out of 5 average rating, 139 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
27 Jul – 1 Aug
4.92 out of 5 average rating, 76 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
1–6 Aug
4.93 out of 5 average rating, 179 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed, 1 bathroom
26–31 Jul
4.99 out of 5 average rating, 157 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
14–19 Aug
4.97 out of 5 average rating, 463 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment
1 bedroom, 1 bed, 1 bathroom
12–17 Jul
4.9 out of 5 average rating, 104 reviews
Guest favourite
Guest suite in Arnold
Coastal Comfort Retreat near Annapolis, EV charger
1 bedroom, 2 beds, 1 bathroom
12–17 Jul
4.94 out of 5 average rating, 215 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
19–24 Jul
4.98 out of 5 average rating, 58 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed, 1 bathroom
9–14 Jul
4.95 out of 5 average rating, 222 reviews
Top guest favourite
Guest house in Annapolis
Guesthouse on The Weems Creek
1 bedroom, 1 queen bed, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 44 reviews
Top guest favourite
Home in Annapolis
Historic Charm | Steps from City Dock and the Yard
2 bedrooms, 4 beds, 2.5 bathrooms
12–17 Jul
4.95 out of 5 average rating, 44 reviews
Top guest favourite
Guest house in Annapolis
Eastport Gem ~ Walk to Downtown Annapolis
1 bedroom, 2 beds, 1.5 bathrooms
12–17 Jul
5.0 out of 5 average rating, 92 reviews
Guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds, 2.5 bathrooms
13–18 Jul
5.0 out of 5 average rating, 13 reviews
Guest favourite
Apartment in Annapolis
Semper Fi Condo
2 bedrooms, 3 queen beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Guest house in Annapolis
Private Art-Filled Guesthouse near Naval Academy
1 bed, 1 bathroom
9–14 Jul
5.0 out of 5 average rating, 171 reviews
Superhost
Home in Annapolis
Tide & Tallow - Walk to Downtown, Main St, Academy
3 bedrooms, 3 beds, 1.5 bathrooms
12–17 Jul
4.74 out of 5 average rating, 35 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 93 reviews
Guest favourite
Flat in Annapolis
NEW lovely studio apartment with onsite parking!
1 bedroom, 1 queen bed, 1 bathroom
12–17 Jul
4.85 out of 5 average rating, 125 reviews