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Search results; Over 1,000 homes in Annapolis

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Guest house in Annapolis
Charming Guest House-Annapolis
1 bedroom, 1 bed, 1 private bathroom
7–12 Sept
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4.8 out of 5 average rating, 30 reviews
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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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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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Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed, 1 bathroom
1–6 Sept
4.98 out of 5 average rating, 164 reviews
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Home in Annapolis
Historic Home w/ Parking Steps From Capital & USNA
1 bedroom, 2 beds, 1.5 bathrooms
10–15 Nov
4.98 out of 5 average rating, 104 reviews
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Flat in Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
1 bedroom, 3 beds, 1 bathroom
12–17 Sept
4.92 out of 5 average rating, 523 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, 40 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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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, 118 reviews
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Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds, WC
3–8 Oct
4.92 out of 5 average rating, 61 reviews
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Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
4.96 out of 5 average rating, 114 reviews
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Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.94 out of 5 average rating, 423 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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Flat in Annapolis
Beautiful Historic Home next to City Dock + USNA
3 bedrooms, 4 beds, 1.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 62 reviews
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Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms, 2 bathrooms
13–18 Sept
4.94 out of 5 average rating, 33 reviews
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Apartment in Annapolis
Captains Quarters | Waterfront & Pool
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 121 reviews
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Place to stay in Annapolis
Guest Suite Getaway near Naval Academy Stadium
1 bed, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 174 reviews
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Cottage in Annapolis
Charming Cottage 2 parking spot easy walk downtown
2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
4.94 out of 5 average rating, 214 reviews