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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
,
4.95 out of 5 average rating, 212 reviews
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Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
21–26 Sept
New place to stay
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Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed, 1 bathroom
4–9 Oct
4.9 out of 5 average rating, 124 reviews
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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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Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 bathroom
4–9 Dec
4.96 out of 5 average rating, 266 reviews
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Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms, 2 bathrooms
25–30 Oct
4.94 out of 5 average rating, 35 reviews
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Home in Edgewater
Water's edge retreat ready to relax with you
2 bedrooms, 2 queen beds, 2 bathrooms
1–6 Nov
New place to stay
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Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 23 reviews
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Top guest favourite
Guest house in Annapolis
Garden View, 1 Bedroom and a Loft.
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 167 reviews
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Home in Annapolis
The 1845 Outpost
3 bedrooms, 3 king beds, 2 bathrooms
20–25 Sept
New place to stay
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Top guest favourite
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, 1139 reviews
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Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
3 bedrooms, 5 beds, 2 bathrooms
29 Sept – 4 Oct
4.99 out of 5 average rating, 70 reviews
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Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds, 1.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 52 reviews
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Home in Pasadena
Bodkin Bay House
4 bedrooms, 5 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Annapolis
4 bedrooms, 7 beds, 3 bath completely updated
4 bedrooms, 7 beds, 3 bathrooms
11–16 Oct
4.97 out of 5 average rating, 146 reviews
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Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 2 beds, 1.5 bathrooms
25–30 Oct
4.93 out of 5 average rating, 94 reviews
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Guest favourite
Home in Arnold
Rachel's BnB
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.9 out of 5 average rating, 153 reviews
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Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 68 reviews
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Flat in Annapolis
Chic 2BR + Den | Annapolis | Sleeps 6
3 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
New place to stay