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Search results; Over 1,000 homes in Annapolis

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Top guest favourite
Apartment in Annapolis
Funky Uptown Apt meets Downtown - Hist District
2 bedrooms, 2 beds, 1 private bathroom
1–6 Oct
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4.96 out of 5 average rating, 128 reviews
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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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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
Home in Annapolis
Walk to Navy Stadium & Shops. No cleaning fee!
3 bedrooms, 4 beds
1–6 Oct
5.0 out of 5 average rating, 37 reviews
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Top guest favourite
Home in Annapolis
Annapolis Charm –Bright 3BR in Downtown
3 bedrooms, 6 beds
4–9 Oct
4.93 out of 5 average rating, 138 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
Cozy Stay in Downtown Naptown
3 bedrooms
25–30 Oct
4.94 out of 5 average rating, 36 reviews
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Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds
1–6 Oct
New place to stay
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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
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds
1–6 Oct
4.98 out of 5 average rating, 46 reviews
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Home in Annapolis
The 1845 Outpost
3 bedrooms, 3 king beds
1–6 Oct
New place to stay
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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, 180 reviews
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Guest favourite
Home in Annapolis
Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
3 bedrooms, 5 beds
1–6 Oct
4.96 out of 5 average rating, 25 reviews
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Top guest favourite
Home in Annapolis
West street historic home
5 bedrooms, 6 beds
4–9 Oct
4.97 out of 5 average rating, 74 reviews
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Guest suite in Annapolis
Annapolis Home 5 miles from Downtown Annapolis
4 bedrooms, 4 beds
1–6 Oct
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
4–9 Oct
4.96 out of 5 average rating, 48 reviews
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Guest favourite
Home in Annapolis
Stay Retro Naptown
4 bedrooms, 4 queen beds
9–14 Nov
4.93 out of 5 average rating, 87 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, 472 reviews
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Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds
4–9 Oct
5.0 out of 5 average rating, 53 reviews