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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 98 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds, 3.5 bathrooms
20–25 Sept
4.91 out of 5 average rating, 92 reviews
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds, 1 bathroom
3–8 Dec
4.97 out of 5 average rating, 460 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
3–8 Oct
4.97 out of 5 average rating, 470 reviews
Top guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 145 reviews
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
27 Sept – 2 Oct
4.96 out of 5 average rating, 172 reviews
Top guest favourite
Home in Annapolis
Historic Home w/ Parking Steps From Capital & USNA
1 bedroom, 2 beds, 1.5 bathrooms
25–30 Oct
4.98 out of 5 average rating, 104 reviews
Top guest favourite
Home in Annapolis
Annapolis waterfront, private pier with kayaks
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
5.0 out of 5 average rating, 45 reviews
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 66 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
20–25 Sept
4.93 out of 5 average rating, 193 reviews
Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds, 2.5 bathrooms
26 Sept – 1 Oct
4.98 out of 5 average rating, 42 reviews
Top guest favourite
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.94 out of 5 average rating, 424 reviews
Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
4.96 out of 5 average rating, 114 reviews
Superhost
Home in Annapolis
Oasis by the Bay - Waterfront Heated Pool Hot Tub!
6 bedrooms, 8 beds, 5 bathrooms
20–25 Sept
4.86 out of 5 average rating, 22 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
20–25 Sept
4.95 out of 5 average rating, 190 reviews
Guest favourite
Bungalow in Annapolis
Light, Bright and Comfortable! No cleaning fee!
3 bedrooms, 3 queen beds, 2 bathrooms
21–26 Sept
4.89 out of 5 average rating, 85 reviews
Guest favourite
Guest suite in Arnold
Captains Quarters Oasis Near Annapolis, Sleeps 4
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
4.95 out of 5 average rating, 214 reviews
Guest favourite
Home in Annapolis
Waterfront Oasis in Eastport-Easy Walk to Downtown
5 bedrooms, 8 beds, 3.5 bathrooms
13–18 Sept
4.93 out of 5 average rating, 123 reviews