Willoway: family-friendly retreat, Pool, 3+ wooded acres
Willoway is the chance to escape that you have been searching for. Built in the 1940’s, it has always been a treasured place for those who lived here or merely visited. In the beginning it was a simple summer cottage in the woods with a pool, that, over the years, was enlarged to become a very comfortable three-bedroom, one-and-a-half bathroom home – all the while retaining its unique character and charm. There is a special energy within its walls, and a sense of peace on its three+ acres of wooded grounds. Come experience what we mean… Willoway awaits. Tucked on a forested hill at the end of a private road in Crotonville, your home-away-from-home (for up to 6 people, and two dogs, if you like) is within easy reach of New York City. Croton-Harmon station is just a five-minute drive from Willoway, and the city is less than an hour’s journey by train… if you want. Wake up in the morning and see how many Willoway bird songs you can recognize. Step out onto the wood or stone decks with your coffee or tea and greet the Willoway sunrise while enveloped by forest and surprising river views. The day is yours, and we want you to make it a good one. Taking a staycation with the family, but still need to go to work in the city sometimes? It’s convenient to do, and you can still be home in time for a cold beverage and a prime Willoway-sunset-viewing seat by the 38,000 gallon seasonally-heated pool. Looking for fun local activities in the surrounding area? There is no shortage of things to do in the beautiful Hudson Valley. Our Willoway Welcome Book will supply you with plenty of ideas. Hiking, history, and local happenings abound, all year long. Just want to decompress at home? We’ve got you. Come “while away at Willoway”. In the summer, float aimlessly in the gorgeous in-ground salt-water pool; nap or read one of our dozens of books in a lounger under an umbrella; or gather at an outdoor table to play one of the many board games available on site (or do the same inside with air-conditioning). In fall and winter, curl up in the large chalet-style living room before a roaring Willoway fire in the enormous stone fireplace and soak in nature’s beauty through the wall of windows beside you; or park yourself at the small table in the kitchen with our bird guide and count how many species come to the feeders on the big tree outside the sliding glass door. In spring, see Mother Nature as she awakens, with spring peepers announcing the new season’s arrival, wild turkeys courting outside your windows (and later marching their little turklets across Willoway’s expanse), and flower bulbs ushering winter away. The whole-house generator will keep you warm or cool, no matter what Mother Nature plans. Willoway will bathe your senses. Enjoy what you see inside, where tastefully updated conveniences are paired with period pieces that remind you of days-gone-by, and art from the four corners of the globe. Relish the outside (including almost half an acre of fenced-in lawn and garden around the pool), which lets your soul slow down and gives you changing nature at your fingertips… hawks and eagles screeching overhead, owls hooting in the dark, cicadas and crickets playing a symphony while fireflies light up the night. Breathe in the scents – flowers and trees in the yard, the comforting smell of logs alight in the fireplace. Feel yourself unwind as colored lights come on in the pool in summer, and you submerge yourself during a late-night dip under the stars. Create delicious meals in the well-appointed kitchen with its induction range, or on the grill (or get take-out from one of many restaurants nearby) and enjoy al-fresco dining beside Japanese maples and towering rhododendrons, or inside-dining in the elegantly decorated dining room with its wall of windows to the backyard. Whether at Willoway with family or friends, good memories are waiting to be created. Right now, as you scroll through various possibilities for your getaway, remember this: life has a way of wearing us all down, and we want to share a special setting that might help build you back up a bit -- where there’s a will, there’s a way. And now that you have read this, you know that there is Willoway. Come see what it can mean for you.
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The host requires you to complete the following before checking out:
Load the dishwasher
Remove personal items
Lock the doors
Pick up after your dog
Failure to complete these may result in a negative review from the host.
Rental agreement and ID verification and security deposit required within 24 hours of booking or booking will be cancelled.
Important information
You need to know
Property # 5105934vb
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, a first aid kit and a deadlock
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
Ossining
Located in Ossining, this holiday home is in a rural area. Van Cortlandt Manor and Sing Sing Correctional Facility are local landmarks, and the area's natural beauty can be seen at Bear Mountain State Park and Old Croton Aqueduct State Park. Ready for a night out? Consider Travelers Rest and Monteverde at Oldstone. Kayaking and windsurfing offer great chances to get out on the surrounding water, or you can seek out an adventure with mountain biking and cycling nearby.
Old Croton Aqueduct State Park - 19 min walk - 1.6 km
Ossining Dog Park - 5 min drive - 2.2 km
Van Cortlandt Manor - 6 min drive - 4.3 km
Bear Mountain State Park - 28 min drive - 29.1 km
Woodbury Common Premium Outlets - 46 min drive - 49.3 km
Getting around
Croton-Harmon Station - 7 min drive
White Plains, NY (HPN-Westchester County) - 36 min drive
Restaurants
Capriccio - 5 min drive
Brothers Fish & Chips - 5 min drive
The Green Growler - 4 min drive
DD's Diner - 4 min drive
Grace Hall - 10 min walk
Frequently asked questions
Does Willoway: family-friendly retreat, Pool, 3+ wooded acres have a pool?
Yes, this property has an outdoor pool. Pool types include heated pools.
How much does it cost to stay at Willoway: family-friendly retreat, Pool, 3+ wooded acres?
As of 18 May, 2026, prices found for a 1-night stay for 2 adults at Willoway: family-friendly retreat, Pool, 3+ wooded acres on 26 May, 2026 start from S$672, 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.
Is Willoway: family-friendly retreat, Pool, 3+ wooded acres pet-friendly?
Yes, this property allows dogs (limit 2 total).
How much is parking at Willoway: family-friendly retreat, Pool, 3+ wooded acres?
On-site parking is available at the property.
What time is check-in at Willoway: family-friendly retreat, Pool, 3+ wooded acres?
Check-in begins at 3:00 PM.
What time is check-out at Willoway: family-friendly retreat, Pool, 3+ wooded acres?
Checkout is at 11:00 AM.
Where is Willoway: family-friendly retreat, Pool, 3+ wooded acres located?
Situated in a rural location, this holiday home is 0.4 mi (0.6 km) from Old Croton Aqueduct State Park and within 3 miles (5 km) of Van Cortlandt Manor and Ossining Public Library. Croton Point Park and Sing Sing Correctional Facility are also within 3 miles (5 km).
About the host
Hosted by Josh Hadden
Josh and Jackie live locally. Josh grew up coming to visit his Uncles place "Willoway" as a kid, and learned to swim in the pool there. When not hosting, they can be found reading books poolside, or planning their next off-the-map adventure.
Why they chose this property
Willoway has been in my family for over 60 years. As a child I did not appreciate how close yet isolated and private it was, nor did the distant Hudson view, or amazing sunsets impress me. Willoway is a place to sidle off to with friends and family to reconnect and have old fashioned fun; reading your own books (or one of many we have seeded throughout the house) around the pool or fireplace, playing one of the dozens of board games. Dining Al fresco, grilling poolside. This is low key luxury, it it is real - not ikea, like the authentic furniture and knick knacks collected over a lifetime. Come find the fascinating history that is part and parcel of Willoway. As one of our reviews noted, it is tended to by people who love it and want to share the place. A 45 minute gorgeous train ride from NYC brings you to a place that encourages you to take a time out from being a New Yorker, to enjoying New York. The lower Hudson River Valley has something for you year round. And Willoway can be your base.
What makes this property unique
Private 3+ acre house, with seasonally heated saltwater pool in a 1/2 acre fenced in yard and garden. Willoway is tucked back up in an area of Ossining that most natives have no idea exists. Yet it is a five minute drive from the major Croton-Harmon Metro-North and Amtrak station. There is an enormous amount of history to explore in the Hudson Valley, and NYC is a 45 minute express train ride away. Or you can just sit by the pool or in front of the fireplace and laze the day away playing one of our board games, or listening to a record.