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Search results; Over 1,000 homes in Annapolis

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Guest favourite
Room in Annapolis
Cozy private room in Annapolis home
1 bedroom, 1 bed, 1 shared bathroom
6–11 Sept
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4.84 out of 5 average rating, 478 reviews
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Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds, 2.5 bathrooms
7–12 Sept
4.93 out of 5 average rating, 14 reviews
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Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed, 1 bathroom
20–25 Sept
4.91 out of 5 average rating, 118 reviews
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Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
2 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
4.87 out of 5 average rating, 75 reviews
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Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 172 reviews
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Superhost
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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Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
10–15 Sept
4.97 out of 5 average rating, 65 reviews
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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, 39 reviews
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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, 225 reviews
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Home in Annapolis
Fleet St Retreat in Downtown - Great Location!
2 bedrooms, 3 beds, 2.5 bathrooms
13–18 Sept
4.91 out of 5 average rating, 123 reviews
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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, 1135 reviews
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Home in Annapolis
Quiet Waterfront
3 bedrooms, 3 beds, 3 bathrooms
6–11 Dec
4.98 out of 5 average rating, 189 reviews
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Hotel room in Annapolis
Historic Inn Stay | 1 Unit | Heart of Annapolis
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
New place to stay
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Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
4 bedrooms, 4 beds, 4 bathrooms
8–13 Sept
5.0 out of 5 average rating, 18 reviews
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Home in Annapolis
Charming on Charles Street
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 33 reviews
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Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 52 reviews
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Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 470 reviews
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Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 18 reviews
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Apartment in Annapolis
Funky Uptown Apt meets Downtown - Hist District
2 bedrooms, 2 double beds, 1 bathroom
8–13 Sept
4.96 out of 5 average rating, 126 reviews