The Whistling Oak
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Craryville
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House
The Whistling Oak is a charming 3 bed, 2.5 bath farmhouse just under 3 hours from NYC. Overlooking a private pond, the home features a cozy woodstove, a screened-in porch ideal for morning coffee or evening wind-downs, and a dedicated workspace for those blending work with getaway. Just a short drive away is Copake Lake, great for relaxation and outdoor adventure.
Nearby towns: Hillsdale (10mins), Claverack (10mins), Copake (15mins), Hudson (20mins), Chatham (20mins), Great Barrington (30mins)
6
3
2.5
Rooms and Beds
Bedroom 1: Master
Bedroom 2
Bedroom 3
Features and Amenities
Rates and Availability
Let Us Find You The Perfect Home!
House Rules
Check-in is at 4pm unless otherwise agreed to in writing.
DEPARTURE
Check-out is by 11am unless otherwise stated in writing. The cleaner will be arriving shortly after to begin preparing for the next renters.
AGE REQUIREMENT
Primary guest booking must be 25 years or older. The person booking should also not have any negative reviews.
PETS
Well-behaved dogs are allowed with prior approval (and $75 fee per pet, per stay). Please clean up after your pet both inside and outside the house. Sorry, cats are not permitted. Failure to disclose any pets in advance may result in additional fees or penalties.
SMOKING
No smoking is permitted inside the house. If you must smoke, please do so outside and dispose of butts properly. Any violation of this policy is subject to a $500 fee.
EXCESSIVE CLEANING FEES
We kindly ask that guests treat the home with care and respect. Should the property require cleaning beyond the standard turnover—due to excessive mess or incidents involving bodily fluids such as blood, vomit, or waste—a $500 fee may apply. Any linens or furnishings damaged beyond repair will also be subject to replacement charges. These situations are considered outside the scope of routine housekeeping and require specialized attention to ensure the safety and well-being of our team.
ACCURATE GUEST COUNT
The number of guests must be accurately disclosed at the time of booking. While we don’t charge extra for additional guests up to the home’s maximum occupancy, this information is essential so we can properly prepare and stock the home. Please note that penalties may apply if guest counts are inaccurate or intentionally misrepresented.
SEPTIC
Please be mindful of the septic system and do not flush anything down the toilets or drains other than toilet paper. This includes any and all personal hygiene products, baby wipes, bleaches and strong chemical cleaners.
BUGS
To avoid unwanted bugs and critters, please do not leave food out or doors open. As well, lyme, a tick-born disease, is a concern in the Hudson Valley and Catskills regions. Please be mindful by wearing long pants and sleeves while hiking or playing outdoors, and remember to check yourself, kids, and pets daily for ticks.
WINTER WEATHER:
In the winter, we recommend a car with four-wheel drive that can handle the snow and slippery roads. While we have someone that plows and salts the roads, weather in the area can be unpredictable so please check and plan accordingly., Not Suitable for Infants. The property is not child friendly., Pets Allowed with Charges, Smoking Not Allowed, Parties not allowed
Location
Price Details
Want to plan further ahead? Join our membership program to unlock the ability to request stays beyond our standard booking dates.
Summary
The Whistling Oak is a charming 3 bed, 2.5 bath farmhouse just under 3 hours from NYC. Overlooking a private pond, the home features a cozy woodstove, a screened-in porch ideal for morning coffee or evening wind-downs, and a dedicated workspace for those blending work with getaway. Just a short drive away is Copake Lake, great for relaxation and outdoor adventure.
Nearby towns: Hillsdale (10mins), Claverack (10mins), Copake (15mins), Hudson (20mins), Chatham (20mins), Great Barrington (30mins)
The Home
The sun-filled living room is designed for gathering and relaxation, with walls of French doors opening to the outdoors, and comfortable seating throughout. Stylish décor and thoughtful touches create an inviting space perfect for curling up with a book, enjoying a fire, or sharing time with family and friends.
The farmhouse-style kitchen boasts marble countertops, chef-worthy appliances, and sunlit windows framing garden views. From easy breakfasts to farm-to-table feasts, this bright space is perfect for creating meals and memories.
Enjoy meals with a view in the charming dining room featuring a large oval table with six light-colored wood chairs positioned in front of a stunning bay window offering picturesque views of the surrounding landscape and built-in bookshelves flanking the window.
Upstairs, you'll find three sunlit bedrooms and two well-appointed bathrooms—one with a tub/shower combination, and the other featuring a walk-in shower. The master bedroom offers a king-size bed, the second bedroom is furnished with a queen-size bed, and the third includes two twin beds.
Step outside to enjoy the peaceful ambiance of the outdoors. Take in serene pond views, unwind in nature, or gather with loved ones for al fresco dining in a truly tranquil setting.
At The Whistling Oak days move at your own pace and the quiet beauty of the surroundings invites you to truly unwind. Whether you're sipping coffee by the pond, sharing meals under the open sky, or simply enjoying the stillness of the trees, this peaceful escape offers the perfect setting to recharge and reconnect.
Notes
Neighborhood
When it’s time to dine, you’re spoiled for choice—North Star, Gaskins, Stissing House, Café Mutton, and Feast & Floret all deliver memorable meals. Planning a picnic? Stock up on artisanal goods at Talbott & Arding or Copake General. For a special dinner, Feast & Floret is not to be missed.
Wine lovers can find the perfect bottle at Fulton & Forbes, while adventurers can rent kayaks or paddleboards from Copake Lake Boat & Ski. Don’t miss a sunset at Olana—absolutely breathtaking. Cap your day with ice cream from Fortunes or a cold pint at Lasting Joy Brewery.
This is a place where small-town charm meets unforgettable experiences—our kind of getaway.