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Chestertown Vacation Rentals

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$1,000+
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12 rentals in Chestertown.
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Retreat at a quiet, water front cottage, vacation rental in Chestertown

Retreat at a quiet, water front cottage

3 bedrooms
3 bathrooms
Sleeps 8
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5 other travelers have booked this property
Water Front Retreat - Sunrise and Sunset Water Views, vacation rental in Chestertown

Water Front Retreat - Sunrise and Sunset Water Views

3 bedrooms
3 bathrooms
Sleeps 8
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Stunning Home on a 25-acre Private Woodland Estate, vacation rental in Chestertown

Stunning Home on a 25-acre Private Woodland Estate

5 bedrooms
5 bathrooms
Sleeps 12
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Cozy & Spacious Chestertown Home, vacation rental in Chestertown

Cozy & Spacious Chestertown Home

4 bedrooms
3 bathrooms
Sleeps 8
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4 other travelers have booked this property
Cottage On Kent, vacation rental in Chestertown

Cottage On Kent

1 bedroom
1 bathroom
Sleeps 3
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1 other traveler has booked this property
Chestertown's Pet-Friendly Little Red Cottage, vacation rental in Chestertown

Chestertown's Pet-Friendly Little Red Cottage

2 bedrooms
1 bathroom
Sleeps 4
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Cottage within walking distance to the Bay!, vacation rental in Chestertown

Cottage within walking distance to the Bay!

1 bedroom
1 bathroom
Sleeps 4
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River Lodge, Casual Riverfront setting, vacation rental in Chestertown

River Lodge, Casual Riverfront setting

4 bedrooms
2 bathrooms
Sleeps 10
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The Rose Cottage - Next to Washington College, vacation rental in Chestertown

The Rose Cottage - Next to Washington College

3 bedrooms
2 bathrooms
Sleeps 3
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First time VRBO Offering!, vacation rental in Chestertown

First time VRBO Offering!

3 bedrooms
2 bathrooms
Sleeps 8
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Wren Retweet-Country Estate in the Center of Chestertown, vacation rental in Chestertown

Wren Retweet-Country Estate in the Center of Chestertown

5 bedrooms
4 bathrooms
Sleeps 10
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Carriage House Hideaway in Middle of Chestertown, vacation rental in Chestertown

Carriage House Hideaway in Middle of Chestertown

1 bedroom
1 bathroom
Sleeps 2
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