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Search results; Over 1,000 homes in Annapolis

Guest favourite
Home in Annapolis
Country House on the Bay
5 bedrooms, 10 beds, 3 private bathrooms
20–25 Jul
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4.9 out of 5 average rating, 224 reviews
Guest favourite
Home in Annapolis
Harbor’s Edge Retreat: Walk to Main St & Academy
3 bedrooms, 3 beds, 1.5 bathrooms
12–17 Jul
4.94 out of 5 average rating, 80 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
19–24 Jul
4.93 out of 5 average rating, 179 reviews
Top guest favourite
Flat in Annapolis
Perfect Eastport location
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
4.98 out of 5 average rating, 144 reviews
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
16–21 Aug
4.96 out of 5 average rating, 157 reviews
Top guest favourite
Home in Annapolis
Gorgeous Historic Downtown Annapolis House
5 bedrooms, 9 beds, 3.5 bathrooms
7–12 Jul
4.98 out of 5 average rating, 155 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed, 1 bathroom
10–15 Aug
4.89 out of 5 average rating, 359 reviews
Top guest favourite
Apartment in Annapolis
Cozy Annapolis Condo
2 bedrooms, 3 beds, 1 bathroom
28 Jul – 2 Aug
4.97 out of 5 average rating, 73 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
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds, 2 bathrooms
30 Jul – 4 Aug
4.96 out of 5 average rating, 111 reviews
Guest favourite
Flat in Annapolis
King George Downtown Annapolis Getaway
2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
4.86 out of 5 average rating, 122 reviews
Top guest favourite
Apartment in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
4.96 out of 5 average rating, 339 reviews
Superhost
Flat in Annapolis
Gybeset Eastport Inn
3 bedrooms, 3 beds, 1 bathroom
7–12 Jul
4.88 out of 5 average rating, 303 reviews
Guest favourite
Guest suite in Arnold
Captains Quarters Oasis Near Annapolis, Sleeps 4
1 bedroom, 2 beds, 1 bathroom
9–14 Jul
4.95 out of 5 average rating, 208 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
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
16–21 Jul
4.92 out of 5 average rating, 74 reviews
Top guest favourite
Home in Annapolis
Marymont Cottage
3 bedrooms, 3 beds, 2 bathrooms
30 Jul – 4 Aug
5.0 out of 5 average rating, 28 reviews
Guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 bathroom
9–14 Jul
4.96 out of 5 average rating, 241 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds, Toilet with sink
7–12 Jul
4.93 out of 5 average rating, 58 reviews