4 Br Private Vacation Home Vacation Rental In Jay, New York

Bring your dogs, pack your skis or Hiking shoes, and leave your laptop open. Oak Hollow Chalet is a classic Adirondack A-frame tucked into the wooded hills of Jay, NY — just 7 miles from Whiteface Mountain and a short drive to the hiking trails, rivers, and farm stands of the High Peaks region. Whether you're here for a ski weekend, a fall foliage escape, or a work-from-the-mountains week, this is your base camp.
The chalet unfolds across three levels with soaring ceilings, warm wood finishes, and the kind of light that makes you want to stay one more night. The centerpiece is the wood-burning fireplace in the main living area — the kind you actually want to sit around after a long day on the mountain. The fully fenced backyard means your dogs have their own adventure while you settle in. There's a dedicated workspace on the upper level — quiet, bright, and far enough from the living room that video calls actually work.
Four bedrooms sleep up to 8 guests comfortably, making this a natural fit for ski crews, families, and friend groups who don't want to feel on top of each other. Two full bathrooms keep mornings running smoothly. The full kitchen is stocked for real cooking — think post-ski pasta nights and Sunday morning pancakes, not just coffee and takeout.
Step outside onto the deck and you've got forest views, fresh air, and enough space to actually use it. Mornings out here with coffee are hard to leave.

Why guests love it
Wood-burning fireplace — the real thing, not a switch
Fully fenced backyard — dogs can run, you can relax
7 miles to Whiteface Mountain — one of the best ski mountains in the East
Dedicated workspace — desk, fast WiFi, natural light
4 bedrooms across 3 levels — space for the whole crew
Private, wooded setting — genuinely quiet

The location
Jay sits at the heart of the Adirondack High Peaks — close enough to everything to feel convenient, far enough away to feel like an escape.
Whiteface Mountain is 7 miles from the front door. Lake Placid — with its restaurants, shops, Olympic museum, and year-round events — is about 16 miles away. The Ausable River runs through the valley below and is one of the best wild trout fisheries in New York State. In summer, it's also a favorite for kayaking and swimming holes.
Fall foliage in the Jay–Whiteface corridor typically peaks in the last two weeks of September and runs into early October. It's one of the most dramatic color displays in the Northeast, and the backroads around Jay are made for slow drives and pulled-over photo stops.
In warmer months, the High Peaks trailheads are 20–40 minutes away. Cascade and Porter are among the most accessible high-peak hikes in the Adirondacks. Wilmington Notch and the Ausable Club area offer everything from easy walks to technical scrambles.
Local picks worth knowing: Hungry Trout Or New Vida Preserve for après drinks, the Ausable Inn or Ice Jam Inn for a proper dinner, and the Keene Farmers Market on summer weekends.

Good to know

Pets welcome (dogs especially) — please bring their gear, we'll have the basics covered
Dedicated workspace with fast WiFi — great for remote work stays of 4+ nights
Wood-burning fireplace — firewood provided seasonally
Full kitchen with all cookware, coffee setup
Private driveway with parking for 3+ vehicles
Self check-in with keypad — arrive whenever works for you
3-night minimum on peak weekends; 2-night minimum otherwise
Please keep dogs in fenced yard or on leash outside fenced area

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Jay is home to this vacation home. Whiteface Mountain and River Stone Wellness are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Tahawus Cultural Center and Santa's Workshop. Dartbrook Rustic Goods and Adirondack Reflections are also worth visiting.