Pine Bush, New York

Your Hudson Valley Oasis

A modern retreat with heated pool, hot tub, and sauna nestled in the Shawangunks — only 1.5 hours from NYC.

4.98
Guest Rating
6
Bedrooms
16+
Guests
108
5-Star Reviews
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Pool and pool house at Winding Trails Hot tub
The Property

Where comfort meets the countryside

Set on a quiet cul-de-sac in Pine Bush, this modern home is the ideal escape for families, friends, and larger gatherings. Swim in the heated pool, unwind in the hot tub, detox in the three-person sauna, or gather around the fire pit under the stars. A full outdoor bar, gas grill, and pizza oven make hosting effortless.

♨
Heated Pool & Hot Tub
Open Apr–Nov
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Indoor Sauna
3-person capacity
🍕
Pizza Oven & Grill
Full outdoor kitchen
🔥
Garden & Fire Pit
Evening gatherings
📶
Fast WiFi
217 Mbps
🐾
Pet Friendly
Small fee applies
Amenities

Everything you need, and more

83 amenities designed for comfort, relaxation, and unforgettable gatherings.

🏊
Heated Pool
Beautiful heated pool with pool house and outdoor bar. Open April through November, weather permitting.
🌊
Hot Tub
Unwind year-round in the hot tub spa, perfectly positioned by the pool house.
🧖‍♀️
Sauna
Three-person indoor sauna for total relaxation and recovery after a day of adventures.
🍳
Full Kitchen
Well-equipped kitchen with everything you need, plus outdoor gas grill and pizza oven.
🔥
Fire Pit & Garden
Beautiful outdoor garden with fire pit, heat lamps, and plenty of room for gathering.
💻
Work & Play
Dedicated workspace, 217 Mbps WiFi, smart lock self check-in, and free parking for 5+ cars.
Sleeping Spaces

6 bedrooms, 4.5 baths

Spacious bedrooms with quality linens and plenty of room for everyone to spread out.

Master bedroom
Master Suite
King Bed
Bonus suite
Bonus Suite
King Bed
Guest bedroom 1
Guest Bedroom
Queen Bed
Guest bedroom 2
Guest Bedroom
Queen Bed
Bunk room
Bunk Room
Full Bunk Bed
Office / bedroom
Office / Flex Room
Queen Sleeper Sofa
Location

Heart of the Shawangunks

Set on a quiet cul-de-sac in Pine Bush, you're perfectly positioned for hiking, wine tasting, family attractions, and seasonal adventure.

  • Minnewaska State Park 20 min
  • Shawangunk Wine Trail 10 min
  • New Paltz 20 min
  • LEGOLAND NY 25 min
  • Holiday Mountain Ski 30 min
  • Kingston 40 min
  • Bear Mountain State Park 40 min
  • West Point 45 min
  • New York City 1.5 hr
Guest Reviews

Loved by every guest

4.98
★★★★★
108 verified reviews
"Absolutely perfect for our family getaway. The pool area is incredible, the hot tub was heavenly, and the house was spotless. Our host was super responsive. We'll definitely be back!"
Recent Guest
★★★★★ · Family Trip
"We hosted a birthday celebration here and it was beyond perfect. The outdoor space with the fire pit, pizza oven, and pool was a dream. The house is even better than the photos."
Recent Guest
★★★★★ · Group Celebration
"A true oasis just 90 minutes from the city. We hiked Minnewaska, explored local wineries, and came home to the hot tub each night. The sauna was a wonderful bonus. Highly recommend!"
Recent Guest
★★★★★ · Weekend Getaway
Book Your Stay

Ready for your escape?

Check availability and book direct. Self check-in with smart lock, Superhost hospitality, and everything you need for an unforgettable stay.

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Common Questions

Frequently asked

How far is Winding Trails from New York City? +

Winding Trails is located in Pine Bush, NY — approximately 1.5 hours from Manhattan via I-87. The drive is scenic and easy, making it perfect for a weekend escape from the city.

When is the pool open? +

The pool is typically open April 1st through November 1st, weather permitting. Heating is included Memorial Day through Labor Day. Before and after that window, pool heating can be requested for an additional fee.

How many guests can Winding Trails accommodate? +

The home sleeps 16+ guests across 6 bedrooms with 7 beds and 4.5 bathrooms. Sleeping arrangements include two king beds, two queen beds, a full bunk bed, and a queen sleeper sofa. Local laws cap the number of adults to 12.

Are pets allowed? +

Yes! Pets are welcome for an additional fee. Please add any pets to your reservation when booking. Undisclosed pets brought without prior approval will incur a $500 fine per pet.

What are the check-in and checkout times? +

Check-in is between 4:00 PM and 10:00 PM via self check-in with a smart lock. Checkout is before 11:00 AM.

What is there to do nearby? +

You're in the heart of the Shawangunks! Minnewaska State Park is 20 minutes away for world-class hiking. The Shawangunk Wine Trail is just 10 minutes out. LEGOLAND NY is 25 minutes, New Paltz is 20, and ski resorts like Holiday Mountain and Mount Peter are 30–45 minutes. Apple picking, antiquing, and seasonal festivals are all close by.

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