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Search results; Over 1,000 homes in Annapolis

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Featured hotel
Hotel in Annapolis
Historic Inns of Annapolis, Governor Calvert king.
1 bedroom, 1 king bed
1–6 Nov
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Home in Annapolis
Charming & Elegant in historic downtown Annapolis
4 bedrooms, 8 beds
12–17 Oct
5.0 out of 5 average rating, 13 reviews
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Guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds
1–6 Oct
4.94 out of 5 average rating, 16 reviews
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Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed
17–22 Oct
5.0 out of 5 average rating, 226 reviews
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Top guest favourite
Guest suite in Annapolis
Cozy Naptown Perch
2 bedrooms, 3 beds
29 Oct – 3 Nov
4.96 out of 5 average rating, 229 reviews
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Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
3–8 Oct
4.97 out of 5 average rating, 473 reviews
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Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
25–30 Oct
4.97 out of 5 average rating, 68 reviews
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Top guest favourite
Home in Annapolis
The Red Door Cottage - Pet-Friendly!
2 bedrooms, 2 beds
16–21 Nov
5.0 out of 5 average rating, 43 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, 268 reviews
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Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds
28 Dec – 2 Jan
4.97 out of 5 average rating, 465 reviews
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Top guest favourite
Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
2 bedrooms, 4 beds
31 Oct – 5 Nov
4.97 out of 5 average rating, 261 reviews
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Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds
4–9 Oct
New place to stay
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Flat in Annapolis
Annapolis Getaway | 2BR Sleeps 6 | Near USNA
3 bedrooms, 2 beds
4–9 Oct
New place to stay
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Top guest favourite
Flat in Annapolis
Elegant Uptown Condo w/Parking
2 bedrooms
26–31 Oct
4.97 out of 5 average rating, 64 reviews
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Top guest favourite
Apartment in Annapolis
Funky Uptown Apt meets Downtown - Hist District
2 bedrooms, 2 beds
1–6 Oct
4.96 out of 5 average rating, 128 reviews
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Guest favourite
Home in Annapolis
Fleet St Retreat in Downtown - Great Location!
2 bedrooms, 3 beds
1–6 Nov
4.91 out of 5 average rating, 125 reviews
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Guest favourite
Home in Annapolis
Beautiful house in the best location!
3 bedrooms, 6 beds
1–6 Oct
4.95 out of 5 average rating, 56 reviews
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Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms
25–30 Oct
4.94 out of 5 average rating, 36 reviews