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Search results; Over 1,000 homes in Annapolis

Guest favourite
Home in Annapolis
Fleet St Retreat in Downtown - Great Location!
2 bedrooms, 3 beds, 2.5 private bathrooms
9–14 Aug
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4.91 out of 5 average rating, 120 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
23–28 Aug
4.93 out of 5 average rating, 80 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed, 1 bathroom
1–6 Aug
4.96 out of 5 average rating, 224 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
4.96 out of 5 average rating, 75 reviews
Top guest favourite
Room in Annapolis
Lovely Private Master Bedroom
1 queen bed, 1 bathroom
1–6 Aug
4.98 out of 5 average rating, 247 reviews
Guest favourite
Home in Arnold
Rachel's BnB
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.91 out of 5 average rating, 138 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms, 2 bathrooms
10–15 Aug
4.94 out of 5 average rating, 31 reviews
Top 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, 16 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
16–21 Aug
4.93 out of 5 average rating, 181 reviews
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
2 bedrooms, 6 beds, 2 bathrooms
10–15 Aug
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds, 2 bathrooms
18–23 Aug
4.96 out of 5 average rating, 111 reviews
Top guest favourite
Guest house in Annapolis
"The Perch" - Hot Tub - Beach - Chesapeake Bay
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.91 out of 5 average rating, 96 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds, WC
1–6 Aug
4.93 out of 5 average rating, 58 reviews
Guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed, 1 bathroom
2–7 Aug
4.96 out of 5 average rating, 131 reviews
Guest favourite
Home in Annapolis
Stay Retro Naptown
4 bedrooms, 4 queen beds, 2 bathrooms
15–20 Sept
4.95 out of 5 average rating, 80 reviews
Top guest favourite
Home in Annapolis
2Bd Water View, w/Beach near Downtown Annapolis
2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 15 reviews
Superhost
Home in Annapolis
*NEW* Pristine, Upscale, Walkable to Town/Stadium
3 bedrooms, 4 beds, 3.5 bathrooms
19–24 Aug
New place to stay
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
15–20 Aug
4.95 out of 5 average rating, 182 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds, 3 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 19 reviews