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Search results; Over 1,000 homes in Annapolis

Guest favourite
Apartment in Annapolis
Anchors Away
Studio, 1 bed, 1 private bathroom
13–18 Sept
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4.84 out of 5 average rating, 109 reviews
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
20–25 Sept
4.97 out of 5 average rating, 67 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds
20–25 Sept
4.91 out of 5 average rating, 92 reviews
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 175 reviews
Top guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds
11–16 Sept
5.0 out of 5 average rating, 147 reviews
Guest favourite
Flat in Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
1 bedroom, 3 beds
12–17 Sept
4.92 out of 5 average rating, 524 reviews
Top guest favourite
Apartment in Annapolis
Funky Uptown Apt meets Downtown - Hist District
2 bedrooms, 2 double beds
11–16 Sept
4.96 out of 5 average rating, 127 reviews
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Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms
13–18 Sept
4.94 out of 5 average rating, 34 reviews
Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds
11–16 Sept
5.0 out of 5 average rating, 52 reviews
Guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds
13–18 Sept
4.93 out of 5 average rating, 15 reviews
Top guest favourite
Home in Annapolis
The Red Door Cottage - Pet-Friendly!
2 bedrooms, 2 beds
29 Nov – 4 Dec
5.0 out of 5 average rating, 42 reviews
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Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds
3–8 Dec
4.97 out of 5 average rating, 462 reviews
Top guest favourite
Home in Annapolis
Charming on Charles Street
3 bedrooms, 4 beds
19–24 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed
17–22 Oct
5.0 out of 5 average rating, 226 reviews
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Guest suite in Annapolis
Cozy Naptown Perch
2 bedrooms, 3 beds
29 Oct – 3 Nov
4.96 out of 5 average rating, 228 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds
1–6 Nov
4.92 out of 5 average rating, 1137 reviews
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Flat in Annapolis
Beautiful Historic Home next to City Dock + USNA
3 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 64 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Annapolis
Southgate Sanctuary - Downtown Annapolis
3 bedrooms, 3 beds
18–23 Sept
4.97 out of 5 average rating, 33 reviews