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Search results showing properties in Annapolis, Maryland, United States of America

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Photo gallery for Amazing views, short walks to great dining!

"The cottage is lovely—vintage charm in perfect combination with the best modern updates. I was comfortable every minute I spent there..." Darcy - June 2021
Premier Host
Cottage · Within West Annapolis

Amazing views, short walks to great dining!

Sleeps 4 · 1 bathroom
10 out of 10 Exceptional (65 reviews)
Unavailable
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Photo gallery for Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

Room
Premier Host
Cottage · 11 min drive to the beach

Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

Sleeps 6 · 3 bedrooms · 1+ bathroom
10 out of 10 Exceptional (20 reviews)
Unavailable
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Photo gallery for Still Available for 2024 Commissioning Week! Dog-friendly beachfront home on the Chesapeake

Welcome to the renovated kitchen at Oh Happy Bay!
Premier Host
Cottage · 6 min drive to the beach

Still Available for 2024 Commissioning Week! Dog-friendly beachfront home on the Chesapeake

Sleeps 8 · 3 bedrooms · 2+ bathrooms
9.8 out of 10 Exceptional (20 reviews)
Unavailable
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Cottage · 9 min drive to the beach

Eastport Cozy Charmer

Sleeps 4 · 2 bedrooms · 2 bathrooms
9.4 out of 10 Exceptional (3 reviews)
Unavailable
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Cottage · 7 min drive to the beach

Coastal Chesapeake cottage in Eastport

Sleeps 7 · 4 bedrooms · 2 bathrooms
10 out of 10 Exceptional (1 review)
Unavailable
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Cottage · 9 min drive to the beach

Secluded Cozy Cottage in Historic Downtown

Sleeps 8 · 2 bedrooms · 1 bathroom
Unavailable
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Cottage · Epping Forest, 4.95 km from Annapolis

Annapolis waterfront "tiny house" in garden setting

Sleeps 4 · 1 bedroom · 1 bathroom
10 out of 10 Exceptional (208 reviews)
Unavailable
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Cottage · Cape Saint Claire, 8.73 km from Annapolis

Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun

Sleeps 5 · 1 bedroom · 1 bathroom
10 out of 10 Exceptional (60 reviews)
Unavailable
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Cottage · 16.48 km from Annapolis

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

Sleeps 3 · 1 bedroom · 1 bathroom
9.8 out of 10 Exceptional (22 reviews)
Unavailable
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Cottage · Hillsmere, 4.68 km from Annapolis

The Yellow Cottage on Harness Creek

Sleeps 6 · 2 bedrooms · 1 bathroom
10 out of 10 Exceptional (137 reviews)
Unavailable
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