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Search results; Over 1,000 homes in Annapolis

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Guest favourite
Guest house in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 bedroom, 1 bed, 1 private bathroom
26–31 Oct
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4.95 out of 5 average rating, 212 reviews
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Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed
4–9 Oct
4.9 out of 5 average rating, 124 reviews
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Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds
4–9 Dec
4.96 out of 5 average rating, 266 reviews
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Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds
21–26 Sept
New place to stay
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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
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Home in Annapolis
The Harness Creek House
6 bedrooms, 6 beds
22–27 Sept
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Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms
25–30 Oct
4.94 out of 5 average rating, 35 reviews
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Guest favourite
Home in Arnold
Rachel's BnB
2 bedrooms, 3 beds
20–25 Sept
4.9 out of 5 average rating, 153 reviews
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Superhost
Home in Annapolis
Annapolis Charmer - Perfect Location
3 bedrooms, 3 beds
27 Sept – 2 Oct
New place to stay
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Top guest favourite
Guest house in Annapolis
Garden View, 1 Bedroom and a Loft.
2 bedrooms, 3 beds
20–25 Sept
4.99 out of 5 average rating, 167 reviews
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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, 23 reviews
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Top guest favourite
Home in Annapolis
Charming on Charles Street
3 bedrooms, 4 beds
19–24 Sept
5.0 out of 5 average rating, 34 reviews
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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, 1139 reviews
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Home in Pasadena
Bodkin Bay House
4 bedrooms, 5 beds
17–22 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Annapolis
Historic + Modern Home | Just Steps to Waterfront
2 bedrooms, 4 beds
20–25 Sept
4.98 out of 5 average rating, 54 reviews
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Top guest favourite
Home in Annapolis
Historic Home w/ Parking Steps From Capital & USNA
1 bedroom, 2 beds
25–30 Oct
4.98 out of 5 average rating, 105 reviews
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Top guest favourite
Guest suite in Annapolis
Cozy Naptown Perch
2 bedrooms, 3 beds
29 Oct – 3 Nov
4.96 out of 5 average rating, 228 reviews
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Top guest favourite
Home in Annapolis
West street historic home
5 bedrooms, 6 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 74 reviews
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Guest favourite
Guest suite in Arnold
Pet-Friendly King Suite + Kitchen | Near Annapolis
1 bedroom, 2 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 216 reviews