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Search results; Over 1,000 homes in Annapolis

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Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
Studio, 2 beds, 1 private bathroom
18–23 Oct
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4.96 out of 5 average rating, 180 reviews
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Home in Annapolis
Charming & Elegant in historic downtown Annapolis
4 bedrooms, 8 beds, 3 bathrooms
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, 2 bathrooms
4–9 Oct
New place to stay
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Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed, 1 bathroom
4–9 Oct
4.9 out of 5 average rating, 126 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
Annapolis Charm –Bright 3BR in Downtown
3 bedrooms, 6 beds, 2 bathrooms
4–9 Oct
4.93 out of 5 average rating, 138 reviews
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Guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
4.94 out of 5 average rating, 16 reviews
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Guest favourite
Home in Annapolis
Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
3 bedrooms, 5 beds, 3.5 bathrooms
1–6 Oct
4.96 out of 5 average rating, 26 reviews
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Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed, 1 bathroom
17–22 Oct
5.0 out of 5 average rating, 226 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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Home in Annapolis
The 1845 Outpost
3 bedrooms, 3 king beds, 2 bathrooms
25–30 Oct
New place to stay
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Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
25–30 Oct
4.97 out of 5 average rating, 68 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
Cozy Stay in Downtown Naptown
3 bedrooms, 2 bathrooms
25–30 Oct
4.94 out of 5 average rating, 36 reviews
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Guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Oct
4.93 out of 5 average rating, 206 reviews
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Home in Annapolis
The Harness Creek House
6 bedrooms, 6 beds, 5 bathrooms
1–6 Oct
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Guest favourite
Home in Severn
Jo’s Luxury Retreat
2 bedrooms, 3 beds, 2 bathrooms
11–16 Oct
5.0 out of 5 average rating, 6 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
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, 46 reviews