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Vacation Rentals in Chestertown, NY and nearby

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All 16 Rentals in the Chestertown Area
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From
$285
Per Night
1 / 6
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Chestertown
4 Bedrooms, 5 Bathrooms, Sleeps 16
Details Reviews (3) Make Inquiry
From
$350
Per Night
1 / 33
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Chestertown
4 Bedrooms, 3 Bathrooms, Sleeps 10
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Details Reviews (5) Make Inquiry
From
$150
Per Night
1 / 24
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Chestertown
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (9) Make Inquiry
From
$125
Per Night
1 / 13
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Chestertown
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
The Black Bear Cabin is a beautiful home privately nestled in the Adirondack State Park on 2 1/2 secluded acres. Located in the Chestertown/Shcroon Lake region, it's the perfect location for a relaxing getaway. The house can accommodate parties of up to 8 people. So whether it's a romantic getaway... View all property information
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5 of 5 stars Reviewed October 16, 2014
We spent a wonderful weekend at Black Bear Cabin. It was much more than what we hoped for. Wonderful getaway without neighbors. Everything was clean and nice, cabin life at it's...
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From
$300
Per Night
1 / 21
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Chestertown
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
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Amenities & Details
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Private Beach
  • Private Fishing...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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 / laundry room. There is a... View all property information
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From
$150
Per Night
1 / 10
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Chestertown
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Grill
  • Mountain Views
  • Private Beach
  • Private Fishing...
  • Safe
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Sitting up high across the street from the Hill Park Association beach, sits this cozy Adirondack camp. You have access to both the beach and a dock, where you can sit back and relax, swim, or catch one of the huge fish Friends Lake is known for. There is a row boat and private dock for your use.... View all property information
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5 of 5 stars Reviewed August 27, 2014
The cabin was cozy in a nice location across from Friend's Lake. The atmosphere was quiet and peaceful and was very relaxing.
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From
$175
Per Night
1 / 12
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Chestertown
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • Wheelchair access
  • Elder access
  • x
About this property
Get your friends or family up to the Lake! This spacious 2 br cabin is perfect for the family, or two couples to relax and get away from it all. Unfortunately, we know you need to connect to the real world, back home, so we've outfitted the cabin with cable TV and wifi internet access. The cabin... View all property information
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From
$175
Per Night
1 / 19
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Chestertown
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (4) Make Inquiry
Amenities & Details
  • Dryer
  • Fireplace
  • Grill
  • Housekeeping...
  • Internet Access
  • Mountain Views
  • Private Beach
  • Private Fishing...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
Rustic and cozy cottage sleeps six with all modern amenities on Friends Lake. Located 30 minutes N of Lake George or about 250 miles N of New York City and 3 hours S of Montreal. Includes 3 fireplaces for cool Adirondack evenings including a field stone outdoor fireplace on the patio. Fully... View all property information
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4 of 5 stars Reviewed July 30, 2014
Everything you need to have a wonderfully relaxing retreat! The cabin is prepared for any sort of relaxing or fun adventure you want: screened porch on the front with hammock...
5 of 5 stars Reviewed July 20, 2014
We had a wonderful time in Chestertown. The location was great, the beach close by and there was something for all ages. We hiked Hadley Mtn. and spent a day at Great Escape. My...
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From
$300
Per Night
1 / 23
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Chestertown
3 Bedrooms, 2 Bathrooms, Sleeps 7
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Garden or Yard
  • Grill
  • Mountain Views
  • Private Beach
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Wake up to the sounds of loons. Have your coffee on the waterfront dock. Adirondack decor, recently remodeled , modern kitchen, huge deck and screened in porch, canoe, kayaks , rownboat View all property information
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From
$300
Per Night
1 / 10
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Chestertown
5 Bedrooms, 5 Bathrooms, Sleeps 8
Bookings
Details Make Inquiry
Amenities & Details
  • Grill
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Relax and unwind at this rustic, cozy Adirondack cabin just steps away from beautiful Crystal Lake. The house was converted from lodging at a former summer resort. Each of the 5 bedrooms has a brand new queen bed. Each room also has a twin bed with a private bathroom and shower. There's a fully... View all property information
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From
$358
Per Night
1 / 19
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Chestertown
5 Bedrooms, 4 Bathrooms, Sleeps 9
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The Murphy House is nestled in the midst of the Adirondacks overlooking the beautiful Friends Lake, and approximately 20 minutes to Gore Mountain. A romantic and rustically elegant place, the Murphy House offers warm and comfortable decor, stone fireplaces, deep soaking tubs, showers, and endless... View all property information
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From
$195
Per Night
1 / 21
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Chestertown
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (5) Make Inquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Housekeeping...
  • Internet Access
  • Mountain Views
  • Private Beach
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
A contemporary salt box style home with 3 bedrooms and 2 baths on two levels make it ideal for several couples vacationing together, a family with children, or an extended family wishing to spend time together, but still provide everyone some privacy.when they choose. What more could you ask for... View all property information
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5 of 5 stars Reviewed November 5, 2014
We met another couple for an extended vacation in the Adirondacks and chose this marvelous retreat as our final week's stay. What a lovely decision it was. We so enjoyed the...
4 of 5 stars Reviewed October 20, 2014
We (my family, 5 adults) stayed here for 2 nights and we all agreed that it was a lovely place. The house is in top condition with an extremely well equipped kitchen (everything...
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The following rentals are within 5 miles of Chestertown, New York.

From
$135
Per Night
1 / 16
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Pottersville
4 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Dryer
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The Annex is a 2 story 1906 Adirondack 'Camp' in the woods located less than 2 1/2 miles off Exit 26 of U.S. I-87, the Adirondack Northway It is available for weekly rental from mid-May through mid-October. In the heart of the Adirondacks, built in 1906 and filled with original art and assorted... View all property information
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5 of 5 stars Reviewed July 20, 2014
Had a wonderful stay at the Annex. A trip back in time, with all the modern conveniences. Highly recommend staying here if visiting the area. Owners Barbara and Clarke made us...
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From
$514
Per Night
1 / 27
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Brant Lake
4 Bedrooms, 4 Bathrooms, Sleeps 10
Booking
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Leisure House with Lake & Mountain Views: Sleeps 8-10, 4 Baths- YEAR ROUND RENTAL Brand New Construction- Rates from $3200-$4500/wk; $500-$700/night in Fall/Winter. 20 mins from GORE MOUNTAIN! Escape to the Adirondack Mountains and the Lake George area without sacrificing your taste for modern... View all property information
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From
$200
Per Night
1 / 9
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Brant Lake
Studio, 2 Bathrooms, Sleeps 7
Details Make Inquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Mountain Views
  • Private Beach
  • Private Fishing...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Four season, four bedroom log cabin in Brant Lake, NY. Located in the south eastern region of Adirondack Park. Hundreds of miles of hiking trails are nearby. Minutes from to I87 - The Northway. Convenient to Fort Ticonderoga, Hague, Bolton Landing, Lake George, and Lake George Village and... View all property information
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From
$250
Per Night
1 / 9
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Pottersville
4 Bedrooms, 2 Bathrooms, Sleeps 9
Details Make Inquiry
Amenities & Details
  • Dryer
  • Garden or Yard
  • Grill
  • Internet Access
  • Mountain Views
  • Private Beach
  • Private Fishing...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
• Located at Wakonda Camping/Cabin community - sleeps 9 with 4 bedrooms, 2 baths, 2 screened in porches, large/private side yard with gas grill/fire pit/picnic table • Steps away from pristine private lake with swimming/canoeing/kayaking/fishing • Schroon River boat launch available w access... View all property information
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Suitability

  • Wheelchair access (0)
  • Elder access (4)
  • Suitable for children (15)
  • Pet friendly (2)
  • Smoking allowed (1)

Amenities

  • Other outdoor space (14)
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  • Internet (11)
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