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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Cape St. Claire
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
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
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
4.89 out of 5 average rating, 360 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Superhost
Flat in Annapolis
Gybeset Eastport Inn
4.88 out of 5 average rating, 303 reviews, 3 bedrooms, 3 beds, 1 bathroom
23–28 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
Top guest favourite
Flat in Annapolis
Perfect Eastport location
4.98 out of 5 average rating, 144 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Guest favourite
Home in Annapolis
Historic Downtown in-law suite
4.96 out of 5 average rating, 242 reviews, 1 bedroom, 2 beds, 1 bathroom
25–30 Oct
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
Home in Annapolis
Gorgeous Historic Downtown Annapolis House
4.98 out of 5 average rating, 155 reviews, 5 bedrooms, 9 beds, 3.5 bathrooms
8–13 Jul
Top guest favourite
Apartment in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
4.96 out of 5 average rating, 340 reviews, 1 bedroom, 2 beds, 1 bathroom
24–29 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
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
4.93 out of 5 average rating, 180 reviews, 1 queen bed, 1.5 bathrooms
24–29 Jul
Top guest favourite
Apartment in Annapolis
Cozy Annapolis Condo
4.97 out of 5 average rating, 73 reviews, 2 bedrooms, 3 beds, 1 bathroom
28 Jul – 2 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
Boat in Annapolis
Welcome Aboard!
4.96 out of 5 average rating, 111 reviews, 2 bedrooms, 3 beds, 2 bathrooms
30 Jul – 4 Aug
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
4.9 out of 5 average rating, 354 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Guest favourite
Flat in Annapolis
King George Downtown Annapolis Getaway
4.86 out of 5 average rating, 122 reviews, 2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
4.93 out of 5 average rating, 58 reviews, 1 bedroom, 2 beds, Toilet with sink
8–13 Jul