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Search results; Over 1,000 homes in Annapolis

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Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
20–25 Sept
4.93 out of 5 average rating, 192 reviews
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Guest suite in Annapolis
Bay View Studio Apartment
2 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 98 reviews
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Guest favourite
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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Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
20–25 Sept
4.95 out of 5 average rating, 190 reviews
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Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
27 Sept – 2 Oct
4.96 out of 5 average rating, 172 reviews
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Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed, 1 bathroom
25–30 Oct
4.91 out of 5 average rating, 119 reviews
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Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 66 reviews
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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, 470 reviews
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Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 145 reviews
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Townhouse in Annapolis
Annapolis Downtown Pleasant St Townhome 3 bedrooms
3 bedrooms, 3 beds, 1.5 bathrooms
6–11 Sept
4.91 out of 5 average rating, 196 reviews
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Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds, 1 bathroom
3–8 Dec
4.97 out of 5 average rating, 460 reviews
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Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds, WC
3–8 Oct
4.87 out of 5 average rating, 62 reviews
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Guest favourite
Flat in Annapolis
The USNA Getaway!
1 bedroom, 3 beds, 1 bathroom
7–12 Sept
4.9 out of 5 average rating, 78 reviews
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Top guest favourite
Room in Annapolis
“Room at the Inn…”
1 queen bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 33 reviews
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Home in Edgewater
Waterfront getaway ready to relax with you
2 bedrooms, 1 queen bed, 2 bathrooms
12–17 Sept
New place to stay
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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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Guest favourite
Bungalow in Annapolis
Light, Bright and Comfortable! No cleaning fee!
3 bedrooms, 3 queen beds, 2 bathrooms
21–26 Sept
4.89 out of 5 average rating, 84 reviews
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Guest favourite
Room in Annapolis
Cozy private room in Annapolis home
1 bed, 1 bathroom
6–11 Sept
4.84 out of 5 average rating, 479 reviews