Whimsy Woods, where contemporary design meets country escape, is a private getaway just minutes from the village of Millbrook. Approaching the property, you’ll feel the rich equestrian history of this historic hamlet, with paddocks and stables, sprawling meadows, and lush lawns. Through the wooden gate, find this uber-private 14-acre estate. The landscape features a mixture of manicured lawns and mature woodlands with walking trails.
The Space:
MAIN HOUSE:
Enter to a light-filled foyer with vaulted ceilings and a stunning chandelier. The glass-paneled stairway and open spaces invite you to explore. A minimalist office with built-in bookcases flows into a formal living room centered around a wood-burning fireplace. Fling open the French doors and invite the breeze while enjoying cocktail hour, or your morning paper.
The opposite side of the main floor is occupied by the kitchen and dining room, with ample seating. The space is open, allowing guests to mingle and pitch in, while you take advantage of the chef’s appliances and generous counter space to conjure a memorable meal. When the weather is right, the patio accessed by French doors off the back is another lovely dining location, with an additional 10-seat dining table under a wisteria-covered pergola and chain of fairy lights.
The main house hosts three bedrooms on the second floor. The primary suite spans one-half of the floor, vaulted ceilings rising to the peak of the roof, separating the bedroom from the expansive primary bath. Light streams through, with a row of glass panels dividing the bed and bath, and windows across both sides of the home. The en-suite bathroom has dual sinks, a walk-in shower, and a lovely soaking tub overlooking the grounds. On the other side of the floor are two guest bedrooms, one with a queen-sized bed, and the other with a pair of single beds and its own dedicated workspace. They share a connected full bathroom between them with a tub/shower.
The basement is a great place to send the kids, or relax for a low-key movie or game night. The media room with built-in bookshelves has a smart TV, comfy couches, a pull out sofa, and a game table. Rounding out the myriad amenities of this home is a home gym with a Peloton bike, treadmill, and assortments of weights and equipment.
GUEST HOUSE:
When you have a full house, take advantage of the guest suite for two above the garage. The open concept suite is divided by a half wall and features a queen bed overlooking the pool, and its own kitchenette. With a sitting area, bistro table and full bath with a walk-in shower this additional space completes Whimsy Wood’s capacity for 8 guests to stay in comfort and style.
Truly, the outdoor spaces set this home apart. The natural cathedral of mature trees surrounding the property gives a sense of total privacy. Wander the trails cut through the woods, and take the kayak out to birdwatch at either of two ponds on the property. The gunite pool surrounded by bluestone patio is an irresistible summer escape. Lounge the day away into the night — the pool is heated — and the propane fire pit will take the edge off an evening chill.
If you can muster the willpower to leave this idyllic property, the town of Millbrook, in the heart of the Hudson Valley, is equally positioned between iconic towns like Rhinebeck and Millerton (both under 30 minutes), and western Litchfield County towns.
Guest Access:
Guests have unrestricted access to the whole property and can enjoy the privacy Whimsy Woods has to offer.
The Neighborhood:
Whimsy Woods is located only 5 minutes away from the Village of Millbrook on one of the town’s most scenic settings, Woodstock Road.
A functioning animal farm offering fresh products for purchase as well as a horseback riding school set on beautiful grounds are neighboring the property.
Getting Around:
The property is set behind a long winding driveway. Ample parking on property. Guests can easily visit the Village of Millbrook via car or bicycle.
Other Things to Note:
Truly, the outdoor spaces set this home apart. The natural cathedral of mature trees surrounding the property gives a sense of total privacy. Wander the trails cut through the woods, and take the kayak out to birdwatch at either of two ponds on the property. The saline gunite pool surrounded by bluestone patio is an irresistible summer escape. Lounge the day away into the night — the pool is heated — and the propane fire pit will take the edge off an evening chill.
If you can muster the willpower to leave this idyllic property, the town of Millbrook, in the heart of the Hudson Valley, is equally positioned between iconic towns like Rhinebeck and Millerton (both under 30 minutes), and western Litchfield County towns.
* Please note the pool opens from mid-to-late May until mid-to-late September. Please inquire regarding specific opening and closing dates.
*One well-behaved dog is welcome at the property (with an additional pet fee). Sorry, cats are not permitted.
Interaction with Guests:
Host will be at guests’ disposal throughout the stay. The guests’ will be supported by local staff to ensure a seamless stay.
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AGE REQUIREMENT
Primary guest booking must be 25 years or older. The person booking should also not have any negative reviews.
PETS
Well-behaved d...
Important information
You need to know
Property # 3390017vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Millbrook
Millbrook is home to this holiday home. Millbrook Vineyards and Winery and Clinton Vineyards are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Buttercup Farm Audubon Sanctuary and James Baird State Park. Innisfree Garden and Trevor Zoo are also worth visiting.
Orvis Sandanona Shooting Grounds - 10 min drive - 6.0 km
Millbrook Vineyards and Winery - 11 min drive - 7.4 km
Institute of Ecosystem Studies - 11 min drive - 8.9 km
Wing's Castle - 13 min drive - 8.9 km
Innisfree Garden - 16 min drive - 12.0 km
Getting around
Poughkeepsie Station - 30 min drive
Newburgh, NY (SWF-Stewart Intl.) - 59 min drive
Restaurants
Stewart's Shops - 13 min drive
Millbrook Continental - 11 min drive
Nooch's - 10 min drive
The Iron Furnace - 16 min drive
House Of Stefas - 11 min drive
Frequently asked questions
Is Whimsy Woods - 14 Acre Millbrook Estate with Pool pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Whimsy Woods - 14 Acre Millbrook Estate with Pool?
As of 9 May 2026, prices found for a 1-night stay for 2 adults at Whimsy Woods - 14 Acre Millbrook Estate with Pool on 8 July 2026 start from NZ$2,919, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Whimsy Woods - 14 Acre Millbrook Estate with Pool?
On-site parking is available at the property.
What time is check-in at Whimsy Woods - 14 Acre Millbrook Estate with Pool?
Check-in begins at 4:00 PM.
What time is check-out at Whimsy Woods - 14 Acre Millbrook Estate with Pool?
Checkout is at 11:00 AM.
Where is Whimsy Woods - 14 Acre Millbrook Estate with Pool located?
Situated in Millbrook, this holiday home is within 6 miles (10 km) of Millbrook Vineyards and Winery, Institute of Ecosystem Studies and Wing's Castle. Innisfree Garden and Clinton Vineyards are also within 9 miles (15 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
We spent Memorial Day weekend at Whimsy Woods and had an amazing time. The house is beautiful, open and so comfortable. The grounds are lush and private with a spectacular pool area and fire pit. Our family and friends had magical dinners to remember. We can’t wait to revisit!