Vacation Rentals Guide

Vacation Rentals in Chestertown

The Official Guide to Vacation Rentals in Chestertown – Your Trusted Source for the Best Stays!

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Chestertown Luxury Vacation Rentals

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10
Excellent
1 Reviews

3 Mi To Washington College! Updated Home W/ Patio

7413 Poplar Ave
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From

793$/night

Pet-Friendly Home On Chester River W/ Dock!

205 Fey Rd
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Walk To Historic Chestertown: Dog-Friendly Retreat

709 High St
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Cheap Chestertown Vacation Rentals

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9.7
Excellent
72 Reviews

From

76$/night

Home Away

7916 Mine Run Road
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8.9
Excellent
226 Reviews

From

80$/night

On Ensor

1309 Ensor Street
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8.9
Excellent
153 Reviews

From

157$/night

Whispering Oak Mansion

3805 Kirkwood Saint Georges Road
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Pet Friendly Vacation Rentals Chestertown Maryland

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7.8
Very good
406 Reviews

From

62$/night

Stylist Bedroom Central Of Baltimore

137 South Central Avenue
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9
Excellent
57 Reviews

From

137$/night

Gaia House

102 Louis Drive
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8.8
Excellent
51 Reviews

From

58$/night

Cozy Room In Baltimore City

41 North Ellamont Street
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Chestertown Vacation Rentals Oceanfront

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10
Excellent
13 Reviews

From

262$/night

Watch Deer From A Farm Cottage

715 Cedar Lane
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9.2
Excellent
27 Reviews

From

194$/night

House On The Gwynns Falls

5017 Wetheredsville Rd
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9.2
Excellent
32 Reviews

From

77$/night

King Suite And Sofa Bed Fast Wi-Fi Easy Dc Access

1705 Berry Ln
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Chestertown Vacation Rentals with Private Pool

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9.4
Excellent
38 Reviews

From

400$/night

Baltimore Abode, Walk To Cross Street Market!

1332 South Hanover Street
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9.5
Excellent
16 Reviews

From

164$/night

Exquisite & Serene 1 Bedroom, 1 Full Bath Apartment

2712 Galeshead Drive
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9.8
Excellent
33 Reviews

Private Studio Apartment With One King Bed And One Sofa Bed

43 Sentry Lane
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8.9
Excellent
19 Reviews

From

73$/night

Lg Cozy Room, Shared Bathroom

41 North Ellamont Street
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9.9
Excellent
11 Reviews

From

338$/night

Adorable 2-Bedroom Bungalow Near Easton, Denton

13508 Tuckahoe Avenue
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9.7
Excellent
14 Reviews

From

365$/night

Vintage Charm: Annapolis Retreat

3 Hill Street
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8.5
Very good
45 Reviews

From

66$/night

Small Cozy Room, Shared Bathroom

41 North Ellamont Street
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Location

Chestertown, Maryland, United States

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