5 Best Vacation Rentals in Chestertown - Holiday Lettings - Cabins

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110 Vacation rentals

(11) Excellent 

15

Chestertown Vacation log cabin rental

New York / Chestertown

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Nearest beach 5 mi
  • Child friendly
  • Private garden
Black Bear Cabin is a beautiful home privately nestled in the southeastern Adirondack State Park on 2 1/2 secluded acres.. It is the perfect location for a relaxing getaway. The house can accommodate 5 guests. Whether it's a romantic getaway for two or a family vacati …see more

from $150 / night

$950 / week

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from $150 / night

(11) Excellent 

34

Cottage rental in Chestertown

New York / Chestertown

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 26 mi
  • Child friendly
Atateka Point Lodge is set on three hundred feet of private lakefront on one of the prettiest private lakes in the Adirondacks. Experience the peace, quiet, and privacy of this end of the road retreat in Valentine Park on Friends Lake. Relax in the 5 person hot tub and …see more

from $400 / night

$3,000 - $3,700 / week

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from $400 / night

(15) Excellent 

25

Chestertown ski apartment to rent.

New York / Chestertown

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Ski
Located in the Southern Adirondack Mountains between Lake George and Gore Mountain Ski Resort our Green Mansions Vacation Condo is the perfect year-round getaway for outdoor lovers, adventure seekers and romantics. Our 2-bedroom, 2-bath home is exceptionally decorated …see more

from $150 / night

$650 - $1,250 / week

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Responds fast!
avg. 3 hours 7 minutes

from $150 / night

9

Vacation home rental

New York / Chestertown

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Air conditioning
  • Pet friendly
Very comfy home in village within walking distance of restaurants, supermarket and post office. We are in the beautiful Adirondacks--about 20 minutes from Lake George, 15 minutes from Schroon Lake and 20 minutes from Gore Mountain. Crib available on request. Full countr …see more

from $160 / night

$900 / week

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from $160 / night

(4) Excellent 

6

Vacation apartment in Chestertown

New York / Chestertown

4 16 2 nights min

  • 4 bedrooms
  • Sleeps 16
  • 2 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning
Elegant apartment rental for 12-16 people. In-town location, central to all Adirondack activities. Weekly rentals at $1995, two-night or weekend rentals at $1495. Apartment boasts a gourmet kitchen, double sided fireplace, spacious great room with flat-screen tv. Gue …see more

from $498 / night

$1,495 - $4,295 / week

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from $498 / night

(17) Excellent 

36

Vacation home in Chestertown

New York / Chestertown

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
After a day enjoying the snow & slopes,come home and relax in front of a blazing fire. Just 15 minutes to Gore Mountain. This is truly a house for all seasons. with activities for everyone. Loon Lake is a crystal clear lake renowned for its watersports and fishing. …see more

from $195 / night

$1,300 - $1,400 / week

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Responds fast!
avg. 2 hours 31 minutes

from $195 / night

(6) Excellent 

Certificate of Excellence

23

B&b rental in Chestertown

New York / Chestertown

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
The Treehouse is a two story guest house located on the shore of Friends Lake in the Adirondacks. One bedroom upstairs with ensuite bathroom and filtered lake views. The first floor includes a living room with full sized futon, a window seat, kitchenette and 1/2 bath / …see more

Certificate of Excellence

from $275 / night

$2,000 - $2,700 / week

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from $275 / night

(1) Excellent 

22

Chestertown Vacation cottage rental

New York / Chestertown

2 7 2 nights min

  • 2 bedrooms
  • Sleeps 7
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
4.5 Stars on VRBO!. The property is totally updated with all new interior, including the kitchen and baths (1 1/2), windows and doors. The home also has a brand new furnace as well as fresh air provided through a heat recycling ventilation system. You will be able to e …see more

from $199 / night

$1,199 - $1,374 / week

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Responds fast!
avg. 1 hour 54 minutes

from $199 / night