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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds, 2 private bathrooms
21–26 Jul
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4.96 out of 5 average rating, 111 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
30 Jul – 4 Aug
4.92 out of 5 average rating, 77 reviews
Top guest favourite
Home in Annapolis
Quiet Waterfront
3 bedrooms, 3 beds, 3 bathrooms
26–31 Jul
4.98 out of 5 average rating, 188 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed, 1 bathroom
1–6 Aug
4.91 out of 5 average rating, 106 reviews
Top guest favourite
Flat in Annapolis
The Sail Loft
3 bedrooms, 4 beds, 2 bathrooms
25–30 Jul
5.0 out of 5 average rating, 36 reviews
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
2 bedrooms, 4 beds, 1.5 bathrooms
23–28 Jul
4.86 out of 5 average rating, 72 reviews
Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4 bedrooms, 6 beds, 3.5 bathrooms
23–28 Aug
4.97 out of 5 average rating, 39 reviews
Guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Aug
4.94 out of 5 average rating, 200 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.92 out of 5 average rating, 1125 reviews
Top guest favourite
Home in Annapolis
Cozy 3BR Annapolis, Private Deck, Parking
3 bedrooms, 3 beds, 2 bathrooms
30 Jul – 4 Aug
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms, 2 bathrooms
19–24 Jul
4.93 out of 5 average rating, 29 reviews
Top guest favourite
Home in Annapolis
Annapolis Charm –Bright 3BR in Downtown
3 bedrooms, 6 beds, 2 bathrooms
1–6 Aug
4.92 out of 5 average rating, 132 reviews
Top guest favourite
Home in Annapolis
Fenced + Fire Pit + Coffee Bar 2 miles from USNA
4 bedrooms, 4 beds, 3 bathrooms
10–15 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Jul
5.0 out of 5 average rating, 13 reviews
Superhost
Flat in Annapolis
Annapolis Adventure 1 block to Harbor @ Gate 1
1 bedroom, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
14–19 Aug
4.97 out of 5 average rating, 463 reviews
Top guest favourite
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
4 bedrooms, 4 beds, 4 bathrooms
16–21 Jul
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Annapolis
Beautiful house in the best location!
3 bedrooms, 6 beds, 3.5 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 47 reviews