The Whistling Oak - Pristine Pond, Tranquility

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) Pets: Allowed (maximum 1). Smoking: Not allowed. Events: Not allowed. Not suitable for children or infants. Reason: The property is not child friendly.. Additional rules: AGE REQUIREMENT Primary guest booking must be 25 years or older. PETS Well-behaved dogs are allowed with prior approval (and $100 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. If you are traveling with a service animal, we kindly ask that you let us know in advance. SMOKING No smoking is permitted inside the house. If you must smoke, please do so outside and dispose of butts properly.. 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. MID-STAY CLEANING REQUIREMENT For stays of 28 nights or longer, a guest-paid mid-stay cleaning is required. The cleaning will be scheduled at a mutually convenient time during your stay. The cost varies by property and will be confirmed before scheduling. 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. OUTSIDE SERVICE PROVIDERS Outside staff such as private chefs, massage therapists, or other service providers are welcome, but prior approval is required before they come on-site. SUPPLEMENTAL AGREEMENTS Guests may be required to sign a rental agreement. If applicable, it will be sent after the booking is confirmed. 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. The Whistling Oak is a charming countryside retreat surrounded by tall pines and lush gardens. This classic home blends timeless character with modern comfort. Start your day with coffee on the screened porch and soak in the peaceful views all around. 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. The Whistling Oak is perfectly placed for exploring the scenic charm of the Hudson Valley. Start your morning with fresh bread from Le Perche in Hudson, then stroll through beautifully curated shops like Finch Hudson and Clove & Creek. For a hands-on floral experience, head to Tiny Hearts Farm to pick your own bouquet. 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.