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Search results; Over 1,000 homes in Annapolis

Descriptions are based on details hosts provide
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 77 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
30 Jul – 4 Aug
Flat in Annapolis
At Home in Naptown
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
15–20 Jul
Top guest favourite
Flat in Annapolis
The Sail Loft
5.0 out of 5 average rating, 36 reviews, 3 bedrooms, 4 beds, 2 bathrooms
25–30 Jul
Guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
4.94 out of 5 average rating, 200 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Aug
Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4.97 out of 5 average rating, 39 reviews, 4 bedrooms, 6 beds, 3.5 bathrooms
23–28 Aug
Top guest favourite
Home in Annapolis
Historic charm near the Naval Academy
4.93 out of 5 average rating, 29 reviews, 3 bedrooms, 2 bathrooms
19–24 Jul
Top guest favourite
Home in Annapolis
Stone fireplace and fire pit in back
5.0 out of 5 average rating, 28 reviews, 3 bedrooms, 3 beds, 2 bathrooms
30 Jul – 4 Aug
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
4.92 out of 5 average rating, 1125 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
4.86 out of 5 average rating, 72 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
23–28 Jul
Top guest favourite
Home in Annapolis
Fenced + Fire Pit + Coffee Bar 2 miles from USNA
5.0 out of 5 average rating, 11 reviews, 4 bedrooms, 4 beds, 3 bathrooms
10–15 Aug
Top guest favourite
Home in Annapolis
Bavarian-themed retreat near the waterfront
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
30 Jul – 4 Aug
Top guest favourite
Home in Annapolis
Annapolis Charm –Bright 3BR in Downtown
4.92 out of 5 average rating, 132 reviews, 3 bedrooms, 6 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 4 beds, 4 bathrooms
16–21 Jul
Top guest favourite
Home in Annapolis
Beautiful house in the best location!
4.96 out of 5 average rating, 47 reviews, 3 bedrooms, 6 beds, 3.5 bathrooms
30 Aug – 4 Sept
Top guest favourite
Home in Annapolis
Waterfront guesthouse with a kayak and pier
4.98 out of 5 average rating, 188 reviews, 3 bedrooms, 3 beds, 3 bathrooms
26–31 Jul
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
4.89 out of 5 average rating, 361 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Top guest favourite
Cottage in Annapolis
Mill Creek views from a wooded porch
4.97 out of 5 average rating, 463 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Aug