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Search results; Over 1,000 homes in Annapolis

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Top guest favourite
Flat in Annapolis
The Sail Loft
3 bedrooms, 4 beds, 2 private bathrooms
4–9 Oct
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5.0 out of 5 average rating, 43 reviews
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Home in Annapolis
Downtown Annapolis House Rental
5 bedrooms, 5 beds, 4 bathrooms
29 Sept – 4 Oct
4.95 out of 5 average rating, 19 reviews
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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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Superhost
Flat in Annapolis
Charming Eastport
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.77 out of 5 average rating, 303 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
Annapolis Charm –Bright 3BR in Downtown
3 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 137 reviews
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Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
21–26 Sept
New place to stay
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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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Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
4.92 out of 5 average rating, 1141 reviews
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Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
3–8 Oct
4.97 out of 5 average rating, 471 reviews
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Top guest favourite
Home in Annapolis
Charming on Charles Street
3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 34 reviews
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Home in Pasadena
Bodkin Bay House
4 bedrooms, 5 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 3 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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Top guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 147 reviews
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Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds, 2.5 bathrooms
26 Sept – 1 Oct
4.98 out of 5 average rating, 45 reviews
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Home in Annapolis
Beautiful 6BR home in Annapolis
6 bedrooms, 6 beds, 4 bathrooms
4–9 Oct
4.64 out of 5 average rating, 70 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
20–25 Sept
4.98 out of 5 average rating, 54 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
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms, 6 beds, 2.5 bathrooms
20–25 Sept
4.94 out of 5 average rating, 33 reviews