Whimsy Woods - 14 Acre Millbrook Estate with Pool

Entire home in Millbrook, New York

  1. 8 guests
  2. 4 bedrooms
  3. 5 beds
  4. 4 baths
Rated 5.0 out of 5 stars.14 reviews
Extraordinary homes, vetted for quality.
Hosted by Red Cottage
  1. Superhost
  2. 13 years hosting

Listing highlights

At-home gym

The treadmill, stationary bike, yoga mat, and free weights are ready for workouts.

Exceptional check-in experience

Recent guests gave the check-in process a 5-star rating.

Unbeatable location

100% of guests in the past year gave this location a 5-star rating.
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.

Other things to note
* Please note the pool opens from mid-to-late May until mid-to-late September. Please inquire regarding specific opening and closing dates.
* The pool is heated up to 75 degrees, complimentary. If you desire additional heating, there is a fee, please inquire for more information. There is a minimum of 2 nights charge for pool heating and the cost ranges from $200-$300 total for pool heating.

*One well-behaved dog is welcome at the property (with an additional pet fee). Sorry, cats are not permitted.

Where you’ll sleep

Bedroom 1
1 queen bed
Bedroom 2
En suite bathroom, 2 single beds
Bedroom 3
En suite bathroom, 1 queen bed

What this place offers

Each Luxe home is fully equipped to meet your needs, with ample space and privacy.
Private outdoor pool - heated, saltwater
Kitchen
Wifi
Free parking on premises
TV

Add-ons

These can be arranged by your host at an additional cost.
Cleaning available during stay

Select check-in date

Add your travel dates for exact pricing

5.0 out of 5 stars from 14 reviews

Overall rating

  1. 5 stars, 100% of reviews
  2. 4 stars, 0% of reviews
  3. 3 stars, 0% of reviews
  4. 2 stars, 0% of reviews
  5. 1 stars, 0% of reviews

Rated 5.0 out of 5 stars for cleanliness

Rated 4.9 out of 5 stars for accuracy

Rated 4.9 out of 5 stars for check-in

Rated 4.9 out of 5 stars for communication

Rated 5.0 out of 5 stars for location

Rated 4.8 out of 5 stars for value

Guest reviews mention

Where you’ll be

Millbrook, New York, United States
This listing's location is verified.

Neighborhood highlights

Whimsy Woods is located only 5 minutes away from the Village of Millbrook on one of the town’s most scenic settings, Woodstock Road.

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. A functioning animal farm offering fresh products for purchase as well as a horseback riding school set on beautiful grounds are neighboring the property.


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.

Meet your host

Superhost
2,801 reviews
4.87 out of 5 average rating
13 years of hosting
Speaks English
Hello! We are Red Cottage, the leading management company for the most exceptional vacation rentals across the Northeast! Our local and friendly team is available 24/7 for guest support needs and available to assist you with any request. Red Cottage properties are known for their thoughtful design and we pride ourselves on our ability to go above and beyond for our guests to ensure an incredible experience. Reach out, we’d love to chat!

Red Cottage is a Superhost

Superhosts are experienced, highly rated hosts who are committed to providing great stays for guests.

Co-hosts

  • Red Cottage

Host details

Response rate: 100%
Responds within an hour
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Things to know

Cancellation policy
House rules
Check-in after 4:00 PM
Checkout before 11:00 AM
8 guests maximum
Safety & property
Exterior security cameras on property
Nearby lake, river, other body of water
Carbon monoxide alarm