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Search results; Over 1,000 homes in Annapolis

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Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed, 1 private bathroom
17–22 Oct
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5.0 out of 5 average rating, 226 reviews
Photo 1 of 29
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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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
Photo 1 of 29
Guest suite in Annapolis
Annapolis Home 5 miles from Downtown Annapolis
4 bedrooms, 4 beds, 4 bathrooms
19–24 Sept
New place to stay
Photo 1 of 29
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
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
Photo 1 of 24
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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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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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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Home in Annapolis
The Harness Creek House
6 bedrooms, 6 beds, 5 bathrooms
30 Sept – 5 Oct
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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
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
Photo 1 of 29
Top guest favourite
Home in Annapolis
Annapolis waterfront, private pier with kayaks
4 bedrooms, 5 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 46 reviews
Photo 1 of 29
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
Photo 1 of 29
Top guest favourite
Cottage in Annapolis
Charming City Retreat. Walk-harbor, eateries.USNA
4 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.87 out of 5 average rating, 118 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
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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
28 Sept – 3 Oct
4.95 out of 5 average rating, 216 reviews