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

Google map showing 44 properties

Photo gallery for Chestertown's Pet-Friendly Little Red Cottage

Exterior
House · 0.8 mi (1.3 km) to Chestertown centre

Chestertown's Pet-Friendly Little Red Cottage

Sleeps 4 · 2 bedrooms · 1 bathroom
Private host
9.8 out of 10 Exceptional (43 reviews)
Unavailable
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Photo gallery for Owl Cottage

Vaulted ceiling great room with staircase to upper loft bedroom with queen bed.
Premier Host
Cottage · 0.5 mi (0.8 km) to Chestertown centre

Owl Cottage

Sleeps 4 · 2 bedrooms · 2 bathrooms
Private host
10 out of 10 Exceptional (10 reviews)
Unavailable
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Photo gallery for Circa 1900 Home in the Heart of Historic Downtown Chestertown

Front Porch
Premier Host
House · 0.7 mi (1.2 km) to Chestertown centre

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Sleeps 6 · 4 bedrooms · 2 bathrooms
Private host
10 out of 10 Exceptional (59 reviews)
Unavailable
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House · 0.7 mi (1.1 km) to Chestertown centre

The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown

Sleeps 8 · 3 bedrooms · 3 bathrooms
Private host
Unavailable
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House · 0.5 mi (0.8 km) to Chestertown centre

Country Estate in Historic District

Sleeps 10 · 5 bedrooms · 3+ bathrooms
Private host
10 out of 10 Exceptional (63 reviews)
Unavailable
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House · 0.7 mi (1.1 km) to Chestertown centre

Beautiful, spacious waterfront home, an easy walk to historic Chestertown

Sleeps 14 · 6 bedrooms · 5+ bathrooms
9.8 out of 10 Exceptional (19 reviews)
Unavailable
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House · 0.9 mi (1.4 km) to Chestertown centre

Historic Stepne Manor on Maryland's Eastern Shore

Sleeps 15 · 5 bedrooms · 3+ bathrooms
10 out of 10 Exceptional (38 reviews)
Unavailable
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House · 0.5 mi (0.8 km) to Chestertown centre

Victorian Hideaway: Beautiful Exterior, Modern interior

Sleeps 8 · 4 bedrooms · 2+ bathrooms
Private host
9.8 out of 10 Exceptional (24 reviews)
Unavailable
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House · 0.6 mi (0.9 km) to Chestertown centre

2 Beds, 2.5 Baths, Perfect Downtown Location

Sleeps 4 · 2 bedrooms · 2+ bathrooms
Private host
10 out of 10 Exceptional (4 reviews)
Unavailable
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House · Chestertown, 8.81 mi from Chestertown

Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities

Sleeps 8 · 3 bedrooms · 3 bathrooms
Private host
10 out of 10 Exceptional (255 reviews)
Unavailable
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House · Chestertown, 2.04 mi from Chestertown

Harbor View Haven | Waterfront w/ Dock + HOT TUB!

Sleeps 10 · 3 bedrooms · 2 bathrooms
10 out of 10 Exceptional (6 reviews)
Unavailable
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House · Chestertown, 1.2 mi from Chestertown

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

Sleeps 6 · 3 bedrooms · 2+ bathrooms
Private host
10 out of 10 Exceptional (1 review)
Unavailable
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House · Chestertown, 1.02 mi from Chestertown

Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

Sleeps 8 · 4 bedrooms · 3 bathrooms
Private host
10 out of 10 Exceptional (84 reviews)
Unavailable
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Cottage · Chestertown, 8.68 mi from Chestertown

Cottage within walking distance to the Bay!

Sleeps 4 · 1 bedroom · 1 bathroom
10 out of 10 Exceptional (5 reviews)
Unavailable
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House · Chestertown, 2.15 mi from Chestertown

Hidden gem with water and golf course views! Bike ride to downtown!

Sleeps 7 · 3 bedrooms · 3 bathrooms
Private host
10 out of 10 Exceptional (25 reviews)
Unavailable
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House · Millington, 12.58 mi from Chestertown

Guest Suite for up to 2 in a Victorian on the Chester River

Sleeps 6 · 1 bedroom · 1 bathroom
Private host
Unavailable
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Cottage · Chestertown, 6.75 mi from Chestertown

Cottage on Chesapeake Eastern Shore on major creek with shared pool and dock.

Sleeps 6 · 3 bedrooms · 2 bathrooms
Private host
Unavailable
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House · Chestertown, 1.55 mi from Chestertown

Breathtaking waterfront home on the Chester River

Sleeps 10 · 4 bedrooms · 4+ bathrooms
10 out of 10 Exceptional (16 reviews)
Unavailable
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