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Search results; Over 1,000 homes in Annapolis

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Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 private bathroom
1–6 Nov
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4.92 out of 5 average rating, 1135 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
Historic Home w/ Parking Steps From Capital & USNA
1 bedroom, 2 beds, 1.5 bathrooms
25–30 Oct
4.98 out of 5 average rating, 104 reviews
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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
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
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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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, 120 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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Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 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 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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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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Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds, 1 bathroom
9–14 Sept
4.94 out of 5 average rating, 145 reviews
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Home in Annapolis
Beautiful house in the best location!
3 bedrooms, 6 beds, 3.5 bathrooms
13–18 Sept
4.94 out of 5 average rating, 52 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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Guest suite in Annapolis
Cozy Naptown Perch
2 bedrooms, 3 beds, 1 bathroom
29 Oct – 3 Nov
4.96 out of 5 average rating, 226 reviews
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Home in Annapolis
Waterfront Oasis in Eastport-Easy Walk to Downtown
5 bedrooms, 8 beds, 3.5 bathrooms
13–18 Sept
4.93 out of 5 average rating, 123 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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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