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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 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 more


Beaver Brook Outfitters

Best day this week by far! Autumn our guide was great and very patient with our kids! We had an exciting ride through the rapids and a tasty 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 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, more


Yankee Boating Center

Clearly the best on Lake George! I compared literally ALL the boat rental companies on LG, and am so glad I did not go with the cheapest. The crew 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 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 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 more


Saddle Up Stables

Great time! Great family fun. It was very relaxing and fun. Nice scenery ride through the Adirondack Mountains and a great view of Lake George. A 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 more


Town of Schroon Public Beach

I didn't know exactly how to find this beach, except that it was supposed to be around the intersection of Route 9 and Dock Street. Driving Northbound 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. 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 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!) 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)

2 reviews write a review

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

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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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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