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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 private bathroom
29 Jul – 3 Aug
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4.92 out of 5 average rating, 1119 reviews
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Flat in Annapolis
Perfect Eastport location
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
4.98 out of 5 average rating, 141 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
19–24 Jul
4.91 out of 5 average rating, 70 reviews
Guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
4.96 out of 5 average rating, 240 reviews
Top guest favourite
Home in Annapolis
Historic + Modern Home | Just Steps to Waterfront
2 bedrooms, 4 beds, 1.5 bathrooms
13–18 Jul
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Home in Annapolis
Marymont Cottage
3 bedrooms, 3 beds, 2 bathrooms
6–11 Jul
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Apartment in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
1 bedroom, 2 beds, 1 bathroom
7–12 Jul
4.96 out of 5 average rating, 338 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
6–11 Jul
4.98 out of 5 average rating, 57 reviews
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
2 bedrooms, 6 beds, 2 bathrooms
5–10 Jul
4.95 out of 5 average rating, 20 reviews
Top guest favourite
Home in Annapolis
DTA Row Home | Walk to City Dock & The Yard
2 bedrooms, 3 beds, 2 bathrooms
11–16 Jul
5.0 out of 5 average rating, 13 reviews
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Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
2 bedrooms, 4 beds, 2 bathrooms
1–6 Jul
4.96 out of 5 average rating, 255 reviews
Top guest favourite
Home in Annapolis
Charming on Charles Street
3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul
5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds, 3.5 bathrooms
5–10 Jul
4.92 out of 5 average rating, 88 reviews
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed, 1 bathroom
16–21 Oct
5.0 out of 5 average rating, 214 reviews
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Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul
4.93 out of 5 average rating, 199 reviews
Top guest favourite
Home in Annapolis
Nautical Luxe Retreat 6 Guests • 3 BDR • 2 Baths
3 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
4.99 out of 5 average rating, 143 reviews
Top guest favourite
Home in Annapolis
Elegant & Authentic Annapolis
1 bedroom, 1 queen bed, 1 bathroom
19–24 Jul
4.99 out of 5 average rating, 147 reviews
Guest favourite
Home in Annapolis
Cozy Cottage
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
4.96 out of 5 average rating, 23 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, 461 reviews