Vacation Rentals & House Rentals in Chestertown

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Wireless Internet
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Pets allowed
Parking
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Beach or lakeside relaxation
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5 Houses

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Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

Wittman log cabin

5 bedrooms
5 bathrooms

sleeps 10

Match: Private outdoor pool (heated)

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Price per night from

$1,117

Tranquil Easton Waterfront Property

Easton house

3 bedrooms
4 bathrooms

sleeps 6

Match: Private outdoor pool (heated)

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Price per night from

$6,870

St. Michael's Premier in Town Summer Cottage now with private pool!

St. Michaels house

2 bedrooms
2 bathrooms

sleeps 4

Match: Private outdoor pool (heated)

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Price per night from

$716

Annapolis Area Shagrila Resort

Davidsonville house

3 bedrooms
3 bathrooms

sleeps 6

Match: Private outdoor pool (heated)

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Price per night from

$916

TRUE ST MICHAELS 6 ACRE WATERFRONT

St. Michaels house

5 bedrooms
3 bathrooms

sleeps 8

Responds fast! avg. 38 minutes

Match: Private outdoor pool (heated)

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Price per night from

$2,295

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Chestertown Rentals

Per night

5 Houses