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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
$140
/ Night
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1 / 13
5 of 5 stars (1) Excellent
Chestertown
3 Bedrooms / 2 Bathrooms / Sleeps 6
travelers have booked this property
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From
$150
/ Night
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1 / 24
5 of 5 stars (9) Excellent
Chestertown
2 Bedrooms / 2 Bathrooms / Sleeps 6
travelers have booked this property
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From
$195
/ Night
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1 / 21
5 of 5 stars (5) Excellent
Chestertown
3 Bedrooms / 2 Bathrooms / Sleeps 8
travelers have booked this property
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From
$150
/ Night
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1 / 10
5 of 5 stars (1) Excellent
Chestertown
2 Bedrooms / 1 Bathroom / Sleeps 4
travelers have booked this property
Overview Reviews (1) Make Inquiry
Amenities & Details
  • Grill
  • Mountain Views
  • 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
$250
/ Night
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1 / 33
5 of 5 stars (5) Excellent
Chestertown
4 Bedrooms / 3 Bathrooms / Sleeps 10
travelers have booked this property
Overview Reviews (5) Make Inquiry
Amenities & Details
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Private Fishing...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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 enjoy the panoramic view of... View all property information
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5 of 5 stars Reviewed October 21, 2014
Atateka Point lodge and guest cottage are located on a beautiful, private lake that is large enough for motor boats and water skiing, but small enough for a nice canoe or kayak...
5 of 5 stars Reviewed October 15, 2014
My family and I had an amazing time. The cottage and treehouse was very nice. The lake was very clear, we wished we could swim, as the beach was sandy, it would be a great summer...
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From
$175
/ Night
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1 / 12
Chestertown
2 Bedrooms / 1 Bathroom / Sleeps 4
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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
$300
/ Night
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1 / 21
Chestertown
2 Bedrooms / 2 Bathrooms / Sleeps 4
travelers have booked this property
Overview Make Inquiry
Amenities & Details
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Private Fishing...
  • Satellite TV
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
$285
/ Night
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1 / 6
5 of 5 stars (3) Excellent
Chestertown
4 Bedrooms / 5 Bathrooms / Sleeps 16
Overview Reviews (3) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Fireplace
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
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. Guest rooms are roomy, all with... View all property information
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5 of 5 stars Reviewed July 21, 2014
Had a meeting here with my sales group worked out great lots of room , great restaurant downstairs . Beaches close to the loft . But the best was the kitchen and dinning room set...
5 of 5 stars Reviewed October 21, 2013
Gorgeous space that has the comforts of home. Perfect spot to gather, make dinner, sit by the fire or having coffee in the morning in a wonderful common area that feels like a...
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From
$175
/ Night
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1 / 19
5 of 5 stars (4) Excellent
Chestertown
3 Bedrooms / 1 Bathroom / Sleeps 6
travelers have booked this property
Overview Reviews (4) Make Inquiry
Amenities & Details
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Mountain Views
  • Private Fishing...
  • Satellite TV
  • Washer
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
/ Night
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1 / 10
Chestertown
5 Bedrooms / 5 Bathrooms / Sleeps 8
travelers have booked this property
Overview Make Inquiry
Amenities & Details
  • Grill
  • Waterfront
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
/ Night
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1 / 19
Chestertown
5 Bedrooms / 4 Bathrooms / Sleeps 9
Overview 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
$300
/ Night
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1 / 23
Chestertown
3 Bedrooms / 2 Bathrooms / Sleeps 7
Overview Make Inquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Mountain Views
  • Washer
  • Waterfront
  • 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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The following rentals are within 5 miles of Chestertown, New York.

From
$514
/ Night
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1 / 27
Brant Lake
4 Bedrooms / 4 Bathrooms / Sleeps 10
traveler have booked this property
Overview Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Mountain Views
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
$250
/ Night
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1 / 9
Pottersville
4 Bedrooms / 2 Bathrooms / Sleeps 9
Overview Make Inquiry
Amenities & Details
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Mountain Views
  • Private Fishing...
  • Satellite TV
  • Washer
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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From
$135
/ Night
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1 / 16
5 of 5 stars (1) Excellent
Pottersville
4 Bedrooms / 1 Bathroom / Sleeps 4
travelers have booked this property
Overview 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... 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
$200
/ Night
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1 / 9
Brant Lake
Studio / 2 Bathrooms / Sleeps 7
Overview Make Inquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Mountain Views
  • Private Fishing...
  • Satellite TV
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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