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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Charming Waterfront Cottage on Historic Property
2 bedrooms, 3 beds, 1.5 private bathrooms
20–25 Oct
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4.95 out of 5 average rating, 65 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 469 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, 85 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds
1–6 Nov
4.92 out of 5 average rating, 1132 reviews
Guest favourite
Home in Annapolis
Nautical Retreat 6 Guests • 3 BDR • 2 Baths
3 bedrooms, 3 beds
22–27 Aug
4.96 out of 5 average rating, 149 reviews
Guest favourite
Guest house in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 bedroom, 1 queen bed
16–21 Aug
4.95 out of 5 average rating, 210 reviews
Top guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
3 bedrooms, 4 beds
16–21 Aug
4.94 out of 5 average rating, 203 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
6–11 Sept
4.98 out of 5 average rating, 63 reviews
Home in Annapolis
DTA - Park and Walk in safe, quiet neighborhood
2 bedrooms, 2 queen beds
16–21 Aug
New place to stay
Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds
21–26 Aug
4.96 out of 5 average rating, 114 reviews
Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
3 bedrooms, 5 beds
16–21 Aug
4.99 out of 5 average rating, 69 reviews
Top guest favourite
Place to stay in Annapolis
Guest Suite Getaway near Naval Academy Stadium
1 bed
16–21 Aug
5.0 out of 5 average rating, 173 reviews
Top guest favourite
Guest house in Stevensville
Private Guesthouse | 7-acres | Near wedding venues
2 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in Annapolis
Large Priv. Suite Near D-town Annapolis & Stadium
1 bedroom, 1 queen bed
16–21 Aug
4.97 out of 5 average rating, 32 reviews
Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed
16–21 Aug
4.9 out of 5 average rating, 50 reviews
Hotel room in Annapolis
Governor Calvert King | Historic Inns
1 bedroom, 1 king bed
23–28 Aug
4.62 out of 5 average rating, 37 reviews
Top guest favourite
Flat in Severna Park
Welcome to Anchors Aweigh!
1 bedroom, 3 beds
19–24 Aug
5.0 out of 5 average rating, 88 reviews
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
2 bedrooms, 4 beds
17–22 Aug
4.86 out of 5 average rating, 74 reviews
Top guest favourite
Guest house in Annapolis
Walk to City Dock & USNA | Designer Eastport Home
2 bedrooms, 3 beds
17–22 Aug
4.98 out of 5 average rating, 44 reviews