Chestertown Vacation Rentals - HolidayHomes base64Hash Chestertown Vacation Rentals - HolidayHomes

Chestertown Vacation Rentals

Browse 71 available vacation homes and compared across 8 trusted partners

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Top-Rated Vacation rentals in Chestertown

Book the highest-rated Chestertown vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Cabin Chestertown
Cottage with BBQ & terrace | Lake view
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Lodge Chestertown
Family-oriented lodge with yard, terrace & BBQ | Good for workation | Pets are welcome
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House Chestertown
Vacation home with barbeque, patio & yard | Mountain view
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House Chestertown
Gorgeous Lakefront Home with a Fire Pit, Two Living Areas, and a Sunroom
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House Chestertown
Adirondack Base Camp by Loon Lake and Gore Mt. !
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House Chestertown
Child-friendly vacation home with patio, yard & jacuzzi | Mountain view
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House Chestertown
NEW for 2024, 6 person hot tub. Spacious country home with large back yard.
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Cabin Chestertown
Deer Crossing, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains
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Cabin Chestertown
Log Haven Cabin, Gore Skiing, Pool/AC/Fireplace, Steps to Loon Lake
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House Chestertown
Vacation home with grill, garden & patio
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Lodge Chestertown
Save on weekly rental & Mon to Thurs. Perfect for Ski Holidays or Summer Fun
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House Chestertown
Children-friendly vacation home with hot tub, private pool & BBQ | Pets are welcome
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House Chestertown
Vacation home with BBQ, patio & yard | Lake view
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House Chestertown
Fairview Cabin, Pool, True Adirondack Cabin steps from Loon Lake
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House Chestertown
Chalet Cabin, Gore Skiing, Pool, AC, Spacious Cabin, Loon Lake
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Top 15 most Recommended Vacation Rentals in Chestertown

Discover your ideal Chestertown vacation rental with real-time comparisons of 71 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Chestertown
House ∙ 6 guests ∙ 4 bedrooms

188 m² House

Chestertown, Chester, New York, United States
This Chestertown house rental accommodates 6 guests and features a cozy fireplace for a warm, inviting atmosphere.
from $242
per night
(45)
View deal
House Chestertown
House ∙ 18 guests ∙ 6 bedrooms

372 m² House

Chestertown, Chester, New York, United States
This spacious house rental in Chestertown accommodates 18 guests and features a private pool for your enjoyment.
from $300
per night
(56)
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House Chestertown
House ∙ 8 guests ∙ 3 bedrooms

120 m² House

Chestertown, Chester, New York, United States
This house rental in Brant Lake accommodates 8 guests and features a cozy fireplace for warm gatherings.
from $305
per night
(25)
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House Chestertown
House ∙ 11 guests ∙ 4 bedrooms

200 m² House

Chestertown, Chester, New York, United States
This house rental in Chestertown accommodates 11 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $351
per night
(4)
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Chalet Chestertown
8 guests ∙ 3 bedrooms

Chalet

Chestertown, Chester, New York, United States
This cozy chalet in Chestertown accommodates 8 guests and features a relaxing hot tub for your enjoyment.
from $494
per night
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House Chestertown
House ∙ 6 guests ∙ 3 bedrooms

138 m² House

Chestertown, Chester, New York, United States
Charming house rental in Chestertown accommodates 6 guests and features a cozy fireplace for a comfortable stay.
from $349
per night
(1)
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Farmhouse Chestertown
Farmhouse ∙ 7 guests ∙ 3 bedrooms

195 m² Farmhouse

Chestertown, Chester, New York, United States
Charming farmhouse rental in Chestertown accommodates 7 guests and features a spacious yard perfect for outdoor activities.
from $290
per night
(4)
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House Chestertown
10 guests ∙ 4 bedrooms

House

Chestertown, Chester, New York, United States
This house rental in Chestertown accommodates 10 guests and features a spacious yard for outdoor enjoyment.
from $620
per night
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Farmhouse Chestertown
Farmhouse ∙ 8 guests ∙ 3 bedrooms

135 m² Farmhouse

Chestertown, Chester, New York, United States
This farmhouse rental in Chestertown accommodates 8 guests and features a cozy fireplace for relaxing evenings.
from $304
per night
(4)
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