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Search results; Over 1,000 homes in Annapolis

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Top guest favourite
Home in Annapolis
Historic + Modern Home | Just Steps to Waterfront
2 bedrooms, 4 beds, 1.5 private bathrooms
20–25 Sept
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4.98 out of 5 average rating, 54 reviews
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Superhost
Home in Annapolis
Waterfront View of Severn, 6 Bedrooms, Sleeps 11
6 bedrooms, 7 beds, 3.5 bathrooms
19–24 Sept
4.83 out of 5 average rating, 6 reviews
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Top guest favourite
Home in Annapolis
Downtown Annapolis House Rental
5 bedrooms, 5 beds, 4 bathrooms
29 Sept – 4 Oct
4.95 out of 5 average rating, 19 reviews
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Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
30 Sept – 5 Oct
New place to stay
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Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
4.89 out of 5 average rating, 373 reviews
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Guest suite in Annapolis
Annapolis Home 5 miles from Downtown Annapolis
4 bedrooms, 4 beds, 4 bathrooms
19–24 Sept
New place to stay
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Top guest favourite
Home in Annapolis
4BR Walk to USNA & Dock · Parking
4 bedrooms, 4 beds, 4 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 18 reviews
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Hotel in Annapolis
3-Star Mystery Hotel Close to US Naval Academy
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
4.5 out of 5 average rating, 28 reviews
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Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds, 2.5 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 229 reviews
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Guest favourite
Room in Annapolis
Laura’s Room
1 double bed, 1 bathroom
20–25 Sept
4.88 out of 5 average rating, 95 reviews
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Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 83 reviews
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Guest favourite
Guest suite in Arnold
Pet-Friendly King Suite + Kitchen | Near Annapolis
1 bedroom, 2 beds, 1 bathroom
21–26 Sept
4.95 out of 5 average rating, 216 reviews
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Hotel room in Annapolis
Governor Calvert King | Historic Inns
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
4.57 out of 5 average rating, 44 reviews
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Top guest favourite
Home in Annapolis
Modern Annapolis Getaway - 2 Free Parking Spaces
2 bedrooms, 2 double beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 122 reviews
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Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 68 reviews
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Guest favourite
Home in Annapolis
Family Oasis|Spa Shower|Near USNA stadium & DTA
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 21 reviews
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Top guest favourite
Home in Annapolis
The Red Door Cottage - Pet-Friendly!
2 bedrooms, 2 beds, 2 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 43 reviews
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Guest favourite
Home in Annapolis
Across from stadium - walk to downtown Annapolis!
4 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
4.9 out of 5 average rating, 136 reviews