Chestertown Vacation Rentals - HolidayHomes base64Hash Chestertown Vacation Rentals - HolidayHomes

Chestertown Vacation Rentals

Browse 68 available vacation homes and compared across 9 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

House Chestertown
Vacation home with barbeque, terrace & yard | Lake view
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House Chestertown
Vacation home with barbeque, patio & yard
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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
Adirondack Base Camp by Loon Lake and Gore Mt. !
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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
Log Haven Cabin, 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
Lake George Hot Tub Firepit Schroon Lake
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House Chestertown
Fairview Cabin, Pool, True Adirondack Cabin steps from Loon Lake
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House Chestertown
House with grill & patio | Perfect for remote work
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Cabin Chestertown
Bass Bunk, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains
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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
2 Minute Walk to the Public Beach! Family and Dog Friendly.
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Top 15 most Recommended Vacation Rentals in Chestertown

Discover your ideal Chestertown vacation rental with real-time comparisons of 67 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 $244
per night
(44)
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 $347
per night
(55)
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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 $181
per night
(21)
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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 $302
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 $295
per night
(4)
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Cabin Chestertown
Cabin ∙ 15 guests ∙ 5 bedrooms

650 m² Cabin

Chestertown, Chester, New York, United States
This spacious cabin in Brant Lake accommodates 15 guests and features a cozy fireplace for warm gatherings.
from $1,646
per night
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House Chestertown
6 guests ∙ 3 bedrooms

House

Chestertown, Chester, New York, United States
Charming house rental in Chestertown for 6, featuring a cozy fireplace and a spacious yard perfect for family gatherings.
from $388
per night
(22)
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Cabin Chestertown
4 guests ∙ 2 bedrooms

Cabin

Chestertown, Chester, New York, United States
This cozy cabin in Chestertown accommodates 4 guests and features a beautiful lakeview for a serene getaway.
from $292
per night
(16)
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Apartment Chestertown
Apartment ∙ 8 guests ∙ 4 bedrooms

244 m² Apartment

Chestertown, Chester, New York, United States
Spacious apartment rental in Chestertown for 8 featuring a cozy fireplace and stunning mountain views.
from $381
per night
(1)
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