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Search results; Over 1,000 homes in Annapolis

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Superhost
Home in Annapolis
Waterfront View of Severn, 6 Bedrooms, Sleeps 11
6 bedrooms, 7 beds, 3.5 bathrooms
18–23 Sept
4.83 out of 5 average rating, 6 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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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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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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Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
18–23 Oct
4.96 out of 5 average rating, 179 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
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds, 3.5 bathrooms
20–25 Sept
4.91 out of 5 average rating, 92 reviews
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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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Guest favourite
Home in Annapolis
The Corner House-Annapolis
3 bedrooms, 5 beds, 2 bathrooms
24–29 Sept
5.0 out of 5 average rating, 7 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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Home in Edgewater
Water's edge retreat ready to relax with you
2 bedrooms, 2 queen beds, 2 bathrooms
1–6 Nov
New place to stay
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Top guest favourite
Home in Annapolis
Historic & sunny home steps from USNA/downtown
3 bedrooms, 5 beds, 2.5 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 204 reviews
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Top guest favourite
Guest house in Annapolis
Guesthouse on The Weems Creek
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 49 reviews
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Guest favourite
Home in Annapolis
Fenced Dog-Friendly Yard 1 Mile to Navy Stadium
4 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.88 out of 5 average rating, 8 reviews
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Home in Annapolis
The Harness Creek House
6 bedrooms, 6 beds, 5 bathrooms
30 Sept – 5 Oct
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Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.9 out of 5 average rating, 51 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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Top guest favourite
Flat in Annapolis
Beautiful Historic Home next to City Dock + USNA
3 bedrooms, 4 beds, 1.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 66 reviews