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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Guest suite in Annapolis
Independent Access Garage Apartment, Near Downtown
1 bedroom, 1 bed, 1 private bathroom
6–11 Jul
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4.89 out of 5 average rating, 429 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
16–21 Jul
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
4.97 out of 5 average rating, 461 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Aug
Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
4.95 out of 5 average rating, 132 reviews, 2 bedrooms, 3 beds, 1 bathroom
20–25 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
CJ's Cottage
4.96 out of 5 average rating, 70 reviews, 2 bedrooms, 3 beds, 2 bathrooms
11–16 Jul
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
4.95 out of 5 average rating, 180 reviews, 1 queen bed, 3 bathrooms
26–31 Jul
Guest favourite
Guest house in Annapolis
"The Perch" - Hot Tub - Beach - Chesapeake Bay
4.9 out of 5 average rating, 92 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
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
19–24 Jul
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
4.93 out of 5 average rating, 179 reviews, 1 queen bed, 1.5 bathrooms
24–29 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
Guest favourite
Apartment in Annapolis
Semper Fi Condo
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 4 beds, 4 bathrooms
9–14 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
Sailing Off Gloucester
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
13–18 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
24–29 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
Hotel room in Annapolis
Governor Calvert King | Historic Inns
4.55 out of 5 average rating, 31 reviews, 1 bedroom, 1 bathroom
16–21 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