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Vacation Rentals in Chestertown, NY and nearby

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    All 15 Rentals in the Chestertown Area
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    From
    $150
    / Night
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    1 / 25
    5 of 5 stars (9) Excellent
    Chestertown
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
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    $200
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    1 / 22
    Chestertown
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travelers have booked this property
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    $250
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    1 / 33
    5 of 5 stars (5) Excellent
    Chestertown
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    travelers have booked this property
    Overview Reviews (5) Make Inquiry
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    1 / 17
    5 of 5 stars (4) Excellent
    Chestertown
    3 Bedrooms / 4 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (4) Make Inquiry
    Amenities & Details
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Private Fishing...
    • Sauna
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • 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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    1 / 20
    5 of 5 stars (2) Excellent
    Chestertown
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Wi-Fi
    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 March 11, 2015
    A lovely cabin with three good size bedrooms. The log burning stove was toasty and the kitchen was supplied with everything you could need. The beds were comfy and...
    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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    $285
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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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    $300
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    1 / 34
    Chestertown
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview Make Inquiry
    Amenities & Details
    • Balcony
    • 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
    “We have lived in this house for more than twenty years, and have many wonderful memories with family and friends. We continue to rent the lake house out to families looking for a place to vacation and to enjoy the natural surroundings with all the comforts of home. We hope you find everything you... View all property information
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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
    Overview Reviews (5) Make Inquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • 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
    Now available during ski season. We are skiers and have kept this gem for ourselves during the winter months, but now for the first time ever, we are accepting winter bookings. Just a 15 minute drive to beautiful, family-friendly Gore Mountain. So come ski during the day and curl up in front a... 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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    $175
    / 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
    • Internet Access
    • Mountain Views
    • Private Fishing...
    • Safe
    • Water Views
    • Wi-Fi
    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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    $175
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    1 / 12
    Chestertown
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • Wheelchair access
    • Elder access
    • x
    • 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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    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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    The following rentals are within 5 miles of Chestertown, New York.

    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
    $514
    / Night
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    1 / 27
    5 of 5 stars (1) Excellent
    Brant Lake
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    traveler have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Pool Table
    • Washer
    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, 4 Baths- YEAR ROUND RENTAL Brand New Construction- Rates from $3500-$4300/wk; $650-$750/night in off season. 20 mins from GORE MOUNTAIN! 15 From Lake George Village. Escape to the Adirondack Mountains and the Lake George area without sacrificing... View all property information
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    5 of 5 stars Reviewed January 9, 2015
    Piya was super helpful throughout the booking process. The house completely surpassed our expectations and we had a wonderful trip.
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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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