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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds, 1 private bathroom
9–15 Sept
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4.95 out of 5 average rating, 137 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
30 Jul – 4 Aug
4.92 out of 5 average rating, 78 reviews
Home in Pasadena
Spacious Family Home in Pasadena
3 bedrooms, 4 beds
17–22 Jul
New place to stay
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds
11–16 Aug
5.0 out of 5 average rating, 27 reviews
Guest favourite
Home in Arnold
Rachel's BnB
2 bedrooms, 3 beds
26–31 Jul
4.91 out of 5 average rating, 137 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 king bed
16–21 Aug
4.9 out of 5 average rating, 355 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
26–31 Jul
4.98 out of 5 average rating, 159 reviews
Top guest favourite
Home in Annapolis
Quaint in the Heart of Annapolis
2 bedrooms, 2 double beds
24–29 Jul
5.0 out of 5 average rating, 114 reviews
Top guest favourite
Guest house in Annapolis
Guesthouse on The Weems Creek
1 bedroom, 1 queen bed
19–24 Jul
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
18–23 Jul
4.97 out of 5 average rating, 463 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed
16–21 Jul
4.96 out of 5 average rating, 223 reviews
Top guest favourite
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
4 bedrooms, 4 beds
19–24 Jul
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Guest house in Annapolis
Private Art-Filled Guesthouse near Naval Academy
1 bed
16–21 Jul
5.0 out of 5 average rating, 171 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed
26–31 Jul
4.95 out of 5 average rating, 182 reviews
Top guest favourite
Home in Annapolis
Villa Annapolitana • Parking 1 min • USNA 4 min
3 bedrooms, 3 beds
18–23 Jul
4.97 out of 5 average rating, 148 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds
19–24 Jul
4.96 out of 5 average rating, 73 reviews
Hotel room in Annapolis
Historic Inn Stay | Steps from Maryland State
1 bedroom, 1 double bed
18–23 Jul
New place to stay
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
1–6 Aug
4.93 out of 5 average rating, 179 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, 12 reviews