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The Whistling Oak - Pristine Pond, Tranquility

3 bedrooms · 4 beds · 2.5 bathrooms · Sleeps 6
HousePet friendly

Where you’ll sleep

Queen
Bedroom 1: Master
Queen
Bedroom 2
2x Twin
Bedroom 3

A charming Hudson Valley farmhouse retreat with private pond views, blending timeless character with modern comfort for a tranquil escape.

  • –Secluded farmhouse retreat overlooking a private pond, just under 3 hours from NYC.
  • –Thoughtfully designed interiors blending classic charm with modern amenities and a dedicated workspace.
  • –An ideal base for exploring the vibrant culinary and outdoor attractions of the Hudson Valley.

The Whistling Oak is a charming 3 bed, 2. 5 bath farmhouse just under 3 hours from NYC.

About this property

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 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 area

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.

The Whistling Oak is just under 3 hours from New York City. A car is essential for getting there and exploring the area. The main access routes are the Taconic State Pkwy, Palisades Interstate Pkwy S and I-87 S. We strongly recommend a 4x4 or a car with four-wheel drive, especially in winter, to handle snow and gravel roads.

full description, the area


Managed by Red Cottage

Red Cottage

New York, NY

4.8★

3,569 reviews

Red Cottage is a vacation rental management company offering curated Catskills, Hudson Valley, Berkshires and Northeast properties with guest services and multi-platform listings.


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Guest Reviews

5.0★ · 8 reviews
★★★★★

“This is my favorite airbnb ever. It's so beautifully decorated and landscaped. It had everything we could need. I can't wait until the calendar opens for next fall so we can book another stay. An absolute dream house and property.”

Guest · Oct 2026

★★★★★

“Highly recommend!”

Feras · Oct 2025

★★★★★

“Beautifully designed home on idyllic property. We felt right at home.”

Guest · May 2026

Good for

Remote workLake daysPets


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Location

Craryville, New York

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