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Hudson Valley Pool Retreat · 50min to NYC · 3 Acre

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A swimming pool with a patio area, surrounded by trees and a sunset view.
A swimming pool with a sunset view, surrounded by trees and a wooden deck.
A swimming pool with a stone wall, outdoor furniture, and a covered seating area.
A wooden cabin with a blue door, a bench, and potted plants.
A poolside patio with a table set for dining, surrounded by chairs and umbrellas.

Reviews

10 out of 10
Exceptional

Highlights

  • Outdoor pool
    The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.
3 bedrooms1+ bathroomSleeps 6

Popular amenities

  • Private pool
  • Onsite parking available
  • Dog-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning

Explore the area

View in a map
Ossining, NY
  • Place, Old Croton Aqueduct State Park
    ‪19 min walk‬
  • Place, Ossining Dog Park
    ‪5 min drive‬
  • Place, Van Cortlandt Manor
    ‪6 min drive‬
  • Airport, White Plains, NY (HPN-Westchester County)
    ‪28 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

2 Single Beds

1 bathroom, 1 half bathroom

Bathroom 1

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Number of living rooms
Garden
Dining area

About this property

Hudson Valley Pool Retreat · 50min to NYC · 3 Acre

Willoway is your private 3+ acre Hudson Valley retreat — a heated 36,000-gallon saltwater pool, distant Hudson River sunset views, and woodland quiet, all 50 minutes from Grand Central by train. Wake to birdsong on the deck, swim until the sky turns orange, dine al fresco for six on the stone patio, and fall asleep by the stone fireplace. Three bedrooms sleep six. Single-level home, gated drive, self check-in, dogs welcome. In my family for 60+ years and still cherished — now yours to enjoy.

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House Rules

Check in after 3:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs (limit 2 total)
Pets are allowed at this property
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Smoking

Smoking allowed: in designated areas
Smoking is allowed at this property

Check-out instructions

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 Registration Number 922770350
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 Rockefeller State Park Preserve. Ready for a night out? Consider Travelers Rest and Dramatic Hall. Kayaking and windsurfing offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking and cycling nearby.
Map
Ossining, NY

What's nearby

  • Old Croton Aqueduct State Park - 19 min walk - 1.6 km
  • Ossining Dog Park - 5 min drive - 2.2 km
  • Croton Point Park - 5 min drive - 3.9 km
  • Van Cortlandt Manor - 6 min drive - 4.3 km
  • Woodbury Common Premium Outlets - 44 min drive - 47.9 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
  • ‪Asagao Sushi - ‬5 min drive

Frequently asked questions

Does Hudson Valley Pool Retreat · 50min to NYC · 3 Acre have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

Is Hudson Valley Pool Retreat · 50min to NYC · 3 Acre pet-friendly?

Yes, this property allows dogs (limit 2 total).

How much is parking at Hudson Valley Pool Retreat · 50min to NYC · 3 Acre?

On-site parking is available at the property.

What time is check-in at Hudson Valley Pool Retreat · 50min to NYC · 3 Acre?

Check-in begins at 3:00 PM.

What time is check-out at Hudson Valley Pool Retreat · 50min to NYC · 3 Acre?

Checkout is at 11:00 AM.

Where is Hudson Valley Pool Retreat · 50min to NYC · 3 Acre located?

Situated in a rural location, this holiday home is within 3 miles (5 km) of Van Cortlandt Manor, Croton Point Park and Louis Engel Waterfront Park. Sing Sing Correctional Facility is 3 mi (4.9 km) away.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 1 out of 1 reviews
Rating 8 - Good. 0 out of 1 reviews
Rating 6 - Okay. 0 out of 1 reviews
Rating 4 - Poor. 0 out of 1 reviews
Rating 2 - Terrible. 0 out of 1 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Debbie L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A dream come true!
Stayed 4 nights in Jun 2026

About the host

Hosted by Josh Hadden

Host profile image
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.
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