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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 beds, 1 private bathroom
30 Aug – 4 Sept
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4.97 out of 5 average rating, 469 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
16–21 Aug
4.93 out of 5 average rating, 187 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, 184 reviews
Hotel room in Annapolis
Historic Inn Stay | Steps from Maryland State
1 bedroom, 1 double bed, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
4.9 out of 5 average rating, 361 reviews
Top guest favourite
Guest house in Edgewater
1 large room efficiency in detached garage.
1 bedroom, 1 queen bed, 1 bathroom
12–17 Sept
4.99 out of 5 average rating, 170 reviews
Top guest favourite
Room in Stevensville
Rustic & Elegant Private Bed & Bath
1 bed, 1 bathroom
9–14 Aug
4.98 out of 5 average rating, 304 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 30 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, 143 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds, WC
7–12 Aug
4.93 out of 5 average rating, 60 reviews
Top guest favourite
Room in Annapolis
A Cottage Room in Presidents Hill
1 single bed, 1.5 bathrooms
15–20 Aug
4.88 out of 5 average rating, 180 reviews
Guest favourite
Rooms in Arnold
Annapolis Room - 3 miles from Naval Academy
2 bedrooms, 3 beds, 1 bathroom
7–12 Aug
4.86 out of 5 average rating, 102 reviews
Top guest favourite
Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
2 bedrooms, 4 beds, 2 bathrooms
17–22 Aug
4.96 out of 5 average rating, 257 reviews
Top guest favourite
Home in Annapolis
Modern Annapolis Getaway - 2 Free Parking Spaces
2 bedrooms, 2 double beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 117 reviews
Guest favourite
Guest house in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 bedroom, 1 queen bed, 1 bathroom
11–16 Aug
4.95 out of 5 average rating, 209 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.96 out of 5 average rating, 224 reviews
Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 bathroom
27 Nov – 2 Dec
4.96 out of 5 average rating, 252 reviews
Guest favourite
Room in Annapolis
French Provincial Suite-Historic Dwntwn Annapolis
1 queen bed, 1.5 bathrooms
7–12 Aug
4.81 out of 5 average rating, 70 reviews
Top guest favourite
Guest house in Annapolis
Private Art-Filled Guesthouse near Naval Academy
1 bed, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 173 reviews