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Search results; Over 1,000 homes in Annapolis

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Top guest favourite
Home in Annapolis
Historic & sunny home steps from USNA/downtown
3 bedrooms, 5 beds, 2.5 private bathrooms
29 Nov – 4 Dec
,
5.0 out of 5 average rating, 204 reviews
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Guest suite in Annapolis
Annapolis Home 5 miles from Downtown Annapolis
4 bedrooms, 4 beds, 4 bathrooms
1–6 Oct
New place to stay
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Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
1–6 Oct
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
1–6 Oct
5.0 out of 5 average rating, 18 reviews
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Home in Annapolis
The 1845 Outpost
3 bedrooms, 3 king beds, 2 bathrooms
1–6 Oct
New place to stay
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Top guest favourite
Room in Annapolis
Guest Suite Getaway near Naval Academy Stadium
1 bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 175 reviews
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Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
8–13 Nov
4.94 out of 5 average rating, 191 reviews
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Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms, 2 bathrooms
25–30 Oct
4.94 out of 5 average rating, 35 reviews
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Guest favourite
Guest suite in Annapolis
The Harness Creek Retreat
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 5 reviews
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Hotel room in Annapolis
Governor Calvert King | Historic Inns
1 bedroom, 1 king bed, 1 bathroom
1–6 Nov
4.57 out of 5 average rating, 44 reviews
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Top guest favourite
Home in Annapolis
Walk to Navy Stadium & Shops. No cleaning fee!
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 37 reviews
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Guest favourite
Guest suite in Arnold
Pet-Friendly King Suite + Kitchen | Near Annapolis
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
4.95 out of 5 average rating, 216 reviews
Photo 1 of 29
Top guest favourite
Home in Annapolis
Annapolis waterfront, private pier with kayaks
4 bedrooms, 5 beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 46 reviews
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Top guest favourite
Home in Annapolis
Historic + Modern Home | Just Steps to Waterfront
2 bedrooms, 4 beds, 1.5 bathrooms
1–6 Oct
4.98 out of 5 average rating, 55 reviews
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Top guest favourite
Home in Annapolis
Downtown Annapolis House Rental
5 bedrooms, 5 beds, 4 bathrooms
1–6 Oct
4.95 out of 5 average rating, 19 reviews
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Home in Annapolis
City Gate Sanctuary
4 bedrooms, 4 beds, 3.5 bathrooms
12–17 Oct
New place to stay
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Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds, 1.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 52 reviews
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Guest favourite
Guest suite in Annapolis
Independent Access Garage Apartment, Near Downtown
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
4.89 out of 5 average rating, 438 reviews
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Guest favourite
Home in Annapolis
Quiet Home Close to Downtown Annapolis and Parks
4 bedrooms, 5 beds, 3 bathrooms
11–16 Oct
4.91 out of 5 average rating, 65 reviews