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Search results; Over 1,000 homes in Annapolis

Guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds, 1 private bathroom
20–25 Sept
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4.94 out of 5 average rating, 147 reviews
Top guest favourite
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, 471 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, 147 reviews
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Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 175 reviews
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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Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 166 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, 226 reviews
Guest favourite
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, 524 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, 462 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, 34 reviews
Top guest favourite
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, 42 reviews
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Apartment in Annapolis
Funky Uptown Apt meets Downtown - Hist District
2 bedrooms, 2 double beds, 1 bathroom
11–16 Sept
4.96 out of 5 average rating, 127 reviews
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Home in Annapolis
Elegant & Authentic Annapolis
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 158 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, 1137 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, 228 reviews
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Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds, 1.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 52 reviews
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Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
2 bedrooms, 2 beds, 1 bathroom
26 Sept – 1 Oct
4.94 out of 5 average rating, 426 reviews
Top guest favourite
Home in Annapolis
Charming on Charles Street
3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
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, 64 reviews