Chestertown Vacation Rentals - HolidayHomes base64Hash Chestertown Vacation Rentals - HolidayHomes

Chestertown Vacation Rentals

Browse 48 available vacation homes and compared across 6 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

We use AI to generate the short summary in each offer below, check full description before booking.
Cabin Chestertown

Cottage with BBQ & terrace | Lake view

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House Chestertown

Adirondack Base Camp by Loon Lake and Gore Mt. !

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House Chestertown

Vacation home with barbeque, patio & yard | Mountain 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

NEW for 2024, 6 person hot tub. Spacious country home with large back yard.

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Cabin Chestertown

Log Haven Cabin, Gore Skiing, Pool/AC/Fireplace, Steps to Loon Lake

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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

< 1 Mi to Beach: Peaceful Brant Lake Home!

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House Chestertown

Vacation home with BBQ, patio & yard | Lake view

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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

Fairview Cabin, Pool, True Adirondack Cabin steps from Loon Lake

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Cabin Chestertown

Deer Run, Gore Mountain, pool, steps from Loon Lake

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House Chestertown

House with pool, barbecue & garden | Lake view

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House Chestertown

House with terrace, jacuzzi & BBQ

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Top 15 most Recommended Vacation Rentals in Chestertown

Discover your ideal Chestertown vacation rental with real-time comparisons of 48 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

We use AI to generate the short summary in each offer below, check full description before booking.
House Chestertown
House โˆ™ 11 guests โˆ™ 4 bedrooms

Children-friendly house with barbeque & patio

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 $295
per night
(5)
View deal
Apartment Chestertown
Apartment โˆ™ 16 guests โˆ™ 4 bedrooms

Big holiday apartment with garden | City view

Chestertown, Chester, New York, United States
This Chestertown apartment rental accommodates 16 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $267
per night
(12)
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Cabin Chestertown
Cabin โˆ™ 15 guests โˆ™ 5 bedrooms

Children-friendly cabin with yard, barbecue & patio

Chestertown, Chester, New York, United States
This spacious cabin in Brant Lake accommodates 15 guests and features a cozy fireplace for warm gatherings.
from $1,521
per night
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House Chestertown
House โˆ™ 7 guests โˆ™ 3 bedrooms

House with grill & patio | Perfect for remote work

Chestertown, Chester, New York, United States
This house rental in Chestertown accommodates 7 guests and features a cozy fireplace for a comfortable stay.
from $265
per night
(34)
View deal
House Chestertown
House โˆ™ 8 guests โˆ™ 4 bedrooms

Family-friendly house with terrace, grill & yard | Nature view

Chestertown, Chester, New York, United States
This house rental in Chestertown accommodates 8 guests and features a cozy fireplace for a comfortable stay.
from $1,015
per night
(59)
View deal
House Chestertown
House โˆ™ 8 guests โˆ™ 3 bedrooms

Fully equipped ample house with sauna & barbeque

Chestertown, Chester, New York, United States
This house rental in Chestertown accommodates 8 guests and features a cozy fireplace for warmth and relaxation.
from $440
per night
(12)
View deal
House Chestertown
House โˆ™ 18 guests โˆ™ 6 bedrooms

Family-oriented vacation home with private pool, terrace & BBQ | City view | Dogs allowed

Chestertown, Chester, New York, United States
This spacious house rental in Chestertown accommodates 18 guests and features a private pool for your enjoyment.
from $386
per night
(62)
View deal
House Chestertown
House โˆ™ 10 guests โˆ™ 4 bedrooms

Family-oriented vacation home with patio, yard & hot tub | Nature view | Good for workation

Chestertown, Chester, New York, United States
This spacious house rental in Horicon accommodates 10 guests and features a cozy fireplace for a warm gathering atmosphere.
from $516
per night
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Chalet Chestertown
Chalet โˆ™ 8 guests โˆ™ 3 bedrooms

Fully equipped chalet with BBQ & hot tub

Chestertown, Chester, New York, United States
This cozy chalet in Chestertown accommodates 8 guests and features a relaxing hot tub for your enjoyment.
from $461
per night
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