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Search results; Over 1,000 homes in Annapolis

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Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds, 2 private bathrooms
26–31 Oct
,
4.97 out of 5 average rating, 116 reviews
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Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
4–9 Oct
4.89 out of 5 average rating, 373 reviews
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Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds
4–9 Dec
4.96 out of 5 average rating, 266 reviews
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Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds
18–23 Oct
4.96 out of 5 average rating, 179 reviews
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Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds
3–8 Dec
4.97 out of 5 average rating, 463 reviews
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Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4 bedrooms, 6 beds
8–13 Nov
4.96 out of 5 average rating, 48 reviews
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Flat in Annapolis
Annapolis Getaway | 2BR Sleeps 6 | Near USNA
3 bedrooms, 2 beds
20–25 Sept
New place to stay
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Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds
30 Sept – 5 Oct
New place to stay
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Guest favourite
Flat in Annapolis
Charming Navy-Themed Townhome | Walk to USNA & DTA
2 bedrooms, 3 beds
28 Sept – 3 Oct
4.93 out of 5 average rating, 118 reviews
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Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
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
28 Sept – 3 Oct
4.95 out of 5 average rating, 216 reviews
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Guest favourite
Room in Annapolis
Laura’s Room
1 double bed
20–25 Sept
4.88 out of 5 average rating, 95 reviews
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Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
8–13 Nov
4.94 out of 5 average rating, 191 reviews
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Top guest favourite
Home in Annapolis
4BR Walk to USNA & Dock · Parking
4 bedrooms, 4 beds
29 Sept – 4 Oct
5.0 out of 5 average rating, 18 reviews
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Top guest favourite
Home in Annapolis
Quiet Waterfront
3 bedrooms, 3 beds
6–11 Dec
4.98 out of 5 average rating, 190 reviews
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Top guest favourite
Cottage in Annapolis
Charming Cottage 2 parking spot easy walk downtown
2 bedrooms, 3 beds
1–6 Nov
4.94 out of 5 average rating, 214 reviews
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Top guest favourite
Guest house in Annapolis
Guesthouse on The Weems Creek
1 bedroom, 1 queen bed
20–25 Sept
5.0 out of 5 average rating, 49 reviews
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Guest favourite
Home in Annapolis
Annapolis Small House in Historic District.
1 bedroom, 2 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 78 reviews
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Guest favourite
Hotel room in Annapolis
Historic Inn Stay | Steps from Maryland State
1 bedroom, 1 double bed
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews