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Vacation Rentals in Chestertown, New York

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about Chestertown

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Chestertown, New York vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Chestertown are added and updated every week!

Compared to hotels, Chestertown vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Chestertown, New York Vacation Rentals and Tourism

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Chestertown things to do

 

Adirondack Extreme Adventure Course

My fiance and I came here for my birthday, and I am SO glad that we did! We both had a blast. Check in was super easy (bonus points for the waiver not being...read more

 

Wildwaters Outdoor Center

Always a pleasurable experience the lodge is super clean and they make everything comfortable. Doug and Aimee have an amazing staff of people. AJ is an...read more

 

Beaver Brook Outfitters

I had a really good time, friendly staff, awesome guide and tasty dinner. I will definitely go back!read more

 

Square Eddy Expeditions

I'm a little bit torn, because when I find such a wonderful "secret", I get nervous sharing it with the rest of the world for fear that they will become so...read more

 

Point O'Pines Camp For Girls

The camp's website sums up this place better than I can as this is a camp "where lifelong friendships are born, confidence is realized, skills are honed,...read more

 

Yankee Boating Center

Quick follow up. After reading this review, Andrew (the owner) gave me a call and apologized for my experience. Didnt get a chance to speak to him, but in...read more

 

Rustic Homestead and Streamside Fly Shop

Took awhile to get a response to book this for my son but he got a 6 hour private lesson from a great guy ( LOU)- he loved it and now hopefully will be...read more

 

Railroads on Parade

Wasn't sure what exactly to expect from a model train exhibit way off the beaten path but glad we made the trip! We took our train loving son here for his...read more

 

Cronin's Golf Resort

Beautiful course, reasonably priced, relaxed atmosphere. I'm a (very) novice golfer, so I won't really be able to compare this place to many others....read more

 

Green Mansion Golf Course

Good course for a novice golfer like myself. Staff are neither friendly nor unfriendly. Some greens are not visible from the tees.read more

 

Saddle Up Stables

My family saw this place as we were driving around the lake and thought it would be cool to stop. A little bit of a wait, but you get to ride on a trail for...read more

 

Ez Storage & Marine

I have been storing a small fishing boat here for the past 5 or 6 years. I was not in the area at the start of the summer and came home in mid-July. I...read more

 

Circle B Ranch

We had a great experience horseback riding. Our guide Joe was great. All the girls setting us up on the horses were nice too! We got there and watched a...read more

 

Strand Theater

The Strand is such an amazing theater. It is truly one of the older theaters in the area. It was closed for a bit and then in the early 90s (I think!) it...read more

 

Schroon Lake-North Hudson Historical Society

This little museum has made great strides since my last review (and it was pretty good then). You could spend a couple days looking at the pictures and...read more

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

Tripp Lake Front House
Chestertown House Rental Picture
  • bedrooms 5
  • community
  • rental type House
  • sleeps 12
  • baths 3
  • rates (USD) $250 - $300 /nt
    $1,450 - $2,950 /wk
 
 
 
 
 

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Adirondack Lake and Gore Ski House Loon Friends & Brant Schroon Lakes Region
Chestertown Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $1,700 /wk
 
 
 
 
 

2 reviews write a review

A Family Friendly, 4 Season Favorite Located On Loon Lake, Near Gore Mountain
Chestertown House Rental Picture
  • bedrooms 6
  • rental type House
  • sleeps 16
  • baths 3
  • rates (USD) $350 /nt
    $2,000 /wk
    $7,000 /mth
 
 
 
 
 

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Mountain Retreat on Private Lake 'Alderbrook Lodge'
Chestertown Lodge Rental Picture
  • bedrooms 8
  • rental type Lodge
  • owner badgeowner badge
  • sleeps 16
  • baths
  • rates (USD) $750 - $857 /nt
    $6,000 /wk
 
 
 
 
 

8 reviews write a review

Large, Historic Adirondack Vacation House with in ground pool and wifi
Chestertown House Rental Picture
  • bedrooms 6
  • rental type House
  • owner badgeowner badge
  • sleeps 20
  • baths 3
  • rates (USD) $750 /nt
    $4,550 /wk
 
 
 
 
 

9 reviews write a review

Beautiful Loon Lake Family Resort In The Adirondack Mountains
Chestertown Lodge Rental Picture
  • bedrooms 6
  • rental type Lodge
  • sleeps 11
  • baths 2
  • rates (USD) $695 /wk
 
 
 
 
 

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