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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
Studio, 1 bed, 1 private bathroom
1–6 Aug
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4.98 out of 5 average rating, 161 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds
15–20 Aug
4.96 out of 5 average rating, 75 reviews
Guest favourite
Home in Arnold
Rachel's BnB
2 bedrooms, 3 beds
16–21 Aug
4.91 out of 5 average rating, 138 reviews
Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds
15–20 Aug
4.97 out of 5 average rating, 39 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
10–15 Aug
4.89 out of 5 average rating, 365 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
23–28 Aug
4.93 out of 5 average rating, 80 reviews
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms, 6 beds
10–15 Aug
4.94 out of 5 average rating, 31 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed
1–6 Aug
4.96 out of 5 average rating, 224 reviews
Top guest favourite
Room in Annapolis
Lovely Private Master Bedroom
1 queen bed
1–6 Aug
4.98 out of 5 average rating, 247 reviews
Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds
18–23 Aug
4.96 out of 5 average rating, 111 reviews
Top guest favourite
Home in Annapolis
2Bd Water View, w/Beach near Downtown Annapolis
2 bedrooms, 3 beds
22–27 Aug
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds
30 Sept – 5 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
24–29 Aug
4.98 out of 5 average rating, 61 reviews
Guest favourite
Home in Annapolis
Peaceful Pet-Friendly Stay | Near USNA & Beaches
3 bedrooms, 5 beds
1–6 Aug
4.9 out of 5 average rating, 21 reviews
Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
3 bedrooms, 5 beds
10–15 Aug
4.98 out of 5 average rating, 66 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
16–21 Aug
4.93 out of 5 average rating, 181 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds
1–6 Aug
4.93 out of 5 average rating, 58 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds
15–20 Aug
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Annapolis
Stay Retro Naptown
4 bedrooms, 4 queen beds
15–20 Sept
4.95 out of 5 average rating, 80 reviews