Chestertown, MD
ASTRO Owners Network — association for short-term rental owners (not a marketplace or OTA)
ASTRO builds a trusted owner network only where short-term rental markets actually work. This destination is part of our verified geography.
Growing Network
27 properties
Properties in Chestertown
Historic Downtown Garden Oasis with Private Patio
unclaimed
Historic Stepne Manor on Maryland's Eastern Shore
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Cedar Point Farm
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Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!
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Victorian Hideaway: Beautiful Exterior, Modern interior
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Country Estate in Historic District
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Pet Friendly Country Estate in Historic District
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Wren Retweet - Villa
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Bed and breakfast
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Victory Farm
unclaimed
Modern Stone Age | Kitchen, Food Lab & Sanctuary (B&B)
unclaimed
The Guesthouse Bed and Breakfast
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White Swan Tavern
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The Lodge at Great Oak Landing
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Brampton 1860
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The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown
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Walk to Historic Chestertown: Dog-Friendly Retreat
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Modern Lux Upstairs apt in Chestertown /Family Friendly /Walk to Shops and Dining!
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Historic luxury townhouse in the heart of downtown Chestertown
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Historic luxury townhouse in the heart of downtown Chestertown
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Circa 1900 Home in the Heart of Historic Downtown Chestertown
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Circa 1900 Home in the Heart of Historic Downtown Chestertown
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Pet Friendly Carriage House Hideaway in Middle of Chestertown
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Down by the River - Charming house on river & walkable to historic Chestertown
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Walk to Historic Chestertown Dog-Friendly Retreat - Vacation Home
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Beautiful, spacious waterfront home, an easy walk to historic Chestertown
unclaimed
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
unclaimed