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Search results; Over 1,000 homes in Annapolis

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Top guest favourite
Home in Annapolis
Elegant & Authentic Annapolis
1 bedroom, 1 bed, 1 private bathroom
25–30 Oct
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4.99 out of 5 average rating, 159 reviews
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Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
1–6 Oct
New place to stay
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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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Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
4.98 out of 5 average rating, 45 reviews
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Top guest favourite
Home in Annapolis
West street historic home
5 bedrooms, 6 beds, 3 bathrooms
4–9 Oct
4.97 out of 5 average rating, 74 reviews
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Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
18–23 Oct
4.96 out of 5 average rating, 179 reviews
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Top guest favourite
Home in Annapolis
Walk to Navy Stadium & Shops. No cleaning fee!
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 37 reviews
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Top guest favourite
Home in Annapolis
The General's House-Spacious Home w/Pool & Hot Tub
4 bedrooms, 7 beds, 4 bathrooms
1–6 Oct
4.96 out of 5 average rating, 46 reviews
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Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds, 1.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 52 reviews
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Guest suite in Annapolis
Annapolis Home 5 miles from Downtown Annapolis
4 bedrooms, 4 beds, 4 bathrooms
1–6 Oct
New place to stay
Photo 1 of 29
Home in Annapolis
The Harness Creek House
6 bedrooms, 6 beds, 5 bathrooms
1–6 Oct
Photo 1 of 29
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, 472 reviews
Photo 1 of 29
Top guest favourite
Home in Annapolis
Fenced + Fire Pit + Coffee Bar 2 miles from USNA
4 bedrooms, 4 beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 18 reviews
Photo 1 of 29
Guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Oct
4.93 out of 5 average rating, 206 reviews
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Guest favourite
Home in Annapolis
Across from stadium - walk to downtown Annapolis!
4 bedrooms, 4 beds, 3 bathrooms
4–9 Oct
4.9 out of 5 average rating, 136 reviews
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Guest favourite
Home in Arnold
Rachel's BnB
2 bedrooms, 3 beds, 1 bathroom
8–13 Nov
4.9 out of 5 average rating, 153 reviews
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Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4 bedrooms, 6 beds, 3.5 bathrooms
8–13 Nov
4.96 out of 5 average rating, 48 reviews
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Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
5–10 Oct
4.93 out of 5 average rating, 195 reviews
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Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds, 1 bathroom
28 Dec – 2 Jan
4.97 out of 5 average rating, 464 reviews