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Search results; Over 1,000 homes in Annapolis

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Guest favourite
Guest suite in Annapolis
Independent Access Garage Apartment, Near Downtown
1 bedroom, 1 bed, 1 private bathroom
20–25 Sept
,
4.89 out of 5 average rating, 437 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
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 bathroom
4–9 Dec
4.96 out of 5 average rating, 266 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
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds, 1 bathroom
3–8 Dec
4.97 out of 5 average rating, 463 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
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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Guest favourite
Flat in Annapolis
Charming Navy-Themed Townhome | Walk to USNA & DTA
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
4.93 out of 5 average rating, 118 reviews
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Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 23 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
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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Flat in Annapolis
Annapolis Getaway | 2BR Sleeps 6 | Near USNA
3 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
New place to stay
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Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4 bedrooms, 6 beds, 3.5 bathrooms
8–13 Nov
4.96 out of 5 average rating, 48 reviews
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Top guest favourite
Cottage in Annapolis
Charming Cottage 2 parking spot easy walk downtown
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.94 out of 5 average rating, 214 reviews
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Guest favourite
Home in Annapolis
Annapolis Small House in Historic District.
1 bedroom, 2 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 78 reviews
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Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed, 1 bathroom
18–23 Oct
4.98 out of 5 average rating, 167 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
Stylish Apt in DTA w/porch&parking
2 bedrooms, 2 beds, 1.5 bathrooms
25–30 Oct
4.93 out of 5 average rating, 95 reviews