Holiday rentals in Upper Jay

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Top-rated holiday rentals in Upper Jay

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
An elevated view captures the cozy retreat nestled among tall green trees. The dark roof contrasts with the vibrant foliage, while a private hot tub is visible on the deck. The property is surrounded by nature, offering a serene atmosphere.
Chalet in Jay
4.96 out of 5 average rating, 310 reviews

Close to Whiteface | Hot Tub | Massage Chair

❄️ Need a winter escape? ❄️ The Place of Prana is a cozy 3-bedroom retreat just 12 minutes from Whiteface and 24 minutes from Lake Placid. Guests come for the adventure but stay for the deep relaxation: ✨ Soak in the hot tub under the stars ✨ Unwind in the massage chair ✨ Spin a record, curl up in the reading nook, and savor peaceful forest views December is for stillness — for cold air, calm mornings, and cozy nights by the fire. Come stay, breathe, and reconnect with yourself and the season.

Top guest favourite
A charming house is showcased in a winter landscape, surrounded by snow-covered trees. The warm glow of light can be seen through the front door, highlighting the stone and wood exterior. Snow blankets the ground, creating a serene, picturesque scene.
Cabin
4.95 out of 5 average rating, 371 reviews

Historic Icehouse in 980 Acres Private Wilderness

The Icehouse is a historic house situated in the High Peaks. The building is surrounded by a stunning private wilderness, with trails, brooks, and fields that no one but guests have access to. As the Park gets more crowded, enjoy undisturbed hiking, back-country skiing, biking, or simply going for picnics to take in some of the best views in the East! The house is very well equipped and has a great kitchen, comfy beds with high-end mattresses and linen, as well as unique furniture and artwork.

Top guest favourite
A queen-sized bed is positioned against a wooden wall with slanted ceilings. Large triangular windows provide views of the surrounding forest and mountains, allowing natural light to fill the space.
Home in Keene
4.97 out of 5 average rating, 193 reviews

Ascent House | Keene

A unique retreat meticulously crafted for resting and recharging after exploring in our beautiful Adirondack Wilderness. Flooded with natural light, every room offers calming frames of nature. Watch the sun peak through the forest and rise over the mountains through expansive windows. Ascend the levels of the house, each revealing more landscape. Experience a designer woodfired traditional Finnish sauna & totally recharge while embracing our harsh Adirondack weather. We hope you love it here.

Top guest favourite
An aerial view of a charming chalet surrounded by lush greenery. A spacious wrap-around deck features outdoor seating and a red umbrella, offering a cozy area for relaxation. Sunlight filters through the trees, enhancing the natural setting.
Chalet in Jay
4.95 out of 5 average rating, 244 reviews

Adirondack Timberwolf Cabin

Cozy Mountain Chalet in Jay, NY on beautiful Glen Road. Only .7 miles to the Jay Covered Bridge, 3 miles to the Jay Mountain summit trail head, 7 miles to Whiteface Mountain, and 16 miles to Lake Placid. Keene and Keene Valley trail heads are only minutes away. The cabin has 3 acres of wooded property with a front driveway as well as a back access drivweway which is nice to walk. There is Satellite TV and wifi. There is good cell coverage. World Class Fishing, Ausable Rivers are close

Top guest favourite
The cabin exterior is illuminated by soft lighting, highlighting the wooden structure surrounded by trees. A cozy fire pit area with red chairs, a picnic table, and an umbrella is visible, creating an inviting outdoor space for relaxation and gathering.
Cabin in Wilmington
4.99 out of 5 average rating, 320 reviews

JUNIPER HILL cabin

Juniper Hill cabin is a new construction two bedroom/one bathroom home situated in Wilmington, NY. This cabin sits in the heart of the Adirondack mountains and is minutes to outdoor adventure of all kinds! Only five minutes to Whiteface Mountain and less than 15 minutes to downtown Lake Placid, the convenience of the location is key for both outdoor enthusiasts and those looking to just getaway and relax in nature. The Ausable River and Lake Everest are both within walking distance.

Top guest favourite
Cabin in Upper Jay
4.95 out of 5 average rating, 338 reviews

Historic River House • Sauna • Warner's Camp

Warner’s Camp is a recently renovated, 1800's guesthouse. The house is located in the Adirondacks High Peaks area, directly adjacent to a freshwater river and swimming hole. Our cabin is perched so close to the river that you can hear and see it from nearly every room. The house is only 10 minutes away from Whiteface Ski Resort, 25 minutes from Lake Placid, and 5 minutes from Keene. Recently featured in Travel + Leisure and Apartment Therapy. Follow us on IG! @warnerscamp

Guest favourite
A scenic view of rolling hills and mountains is captured at sunset, with soft hues of orange and pink in the sky. In the foreground, sheep graze peacefully on vibrant green grass, framed by a rustic structure and a hint of electrified fence.
Tiny home in Jay
4.94 out of 5 average rating, 509 reviews

The Shepherd's Crook at Blue Pepper Farm

Tucked in the woods on our working sheep farm, our off-grid tiny house is the perfect escape and stepping stone into the Adirondack mountains for hiking, skiing, and snowshoeing. Enjoy the coziness of the Crook between forays into our north country wilderness! What you will find: adventure, peace, quiet, woodstove, candles, down blanket, fire pit, privacy, composting outhouse, firewood for sale. **Please note there is NO electricity and NO running water. Akin to glamping!

Top guest favourite
A sprawling meadow extends towards distant mountains, with a varied landscape marked by trees and fields. The sky is partially covered with clouds, offering a serene view of the natural surroundings and hints of autumn colors in the foliage.
Home in Wilmington
4.95 out of 5 average rating, 519 reviews

THE VIEW! THE VIEW! THE VIEW!

A 1900 farmhouse that has been in the family for generations. Recently renovated to accommodate up to 5 guests, it is clean with simple furnishings and a SPECTACULAR VIEW! Located RIGHT ON NYS RTE 86 (close to the road) with easy access to nearby attractions. The house is split in 2 and is designed for 2 families. I rent out "The View" using airbnb exclusively. My wife and I reside in the back portion of the house with a separate entrance and separate parking.

Top guest favourite
Place to stay in Upper Jay
5 out of 5 average rating, 132 reviews

Lewis Brook Lodge

Nestled in the Adirondack Mountains, this 1860 farmhouse is just10 minutes to Whiteface mountain , and 25 minutes to Lake Placid! Breakfast foods are included with your stay. Enjoy evenings around the fire pit, cocktails by the koi pond or relax in the ADK chairs next to Lewis Brook. We are walking distance to The Ice Jam, Adirondack Mountain Coffee, Sugar House Creamery, Recovery Lounge , post office and a library. NEW NEW NEW SALTWATER HOT TUB, very private.

Guest favourite
Home in Upper Jay
4.95 out of 5 average rating, 104 reviews

Whiteface Holiday: Hot Tub, Ski, Family Memories!

Forge unforgettable winter memories at Sugar House ADK Base Camp! Enjoy majestic, snow-covered views with family (pets included!) and friends. Just 9 min from Whiteface skiing and 23 min to Lake Placid. Sip hot cocoa or coffee made your way outside in the hot tub or inside by the fireplace after a day on the slopes. This contemporary farmhouse features a full kitchen and a huge game room with ping pong, billiards, and poker for cozy nights in.

Top guest favourite
An A-frame cabin stands under a starry night sky, with large glass doors illuminating the interior. Outdoor string lights create a warm glow along the path leading to the cabin, surrounded by trees and natural landscape.
Cabin in Jay
4.99 out of 5 average rating, 143 reviews

Aframe - Sauna, Near Lake Placid - Unique & Modern

Welcome to ADK Aframe - A luxury mid-century modern cabin! Located on a quiet road, this amazing space serves as a relaxing retreat for you to recharge after adventure filled days hiking, biking, paddling, fishing and skiing. Our pet-free home features all new furnishings and modern comforts, including a barrel sauna. The neighborhood includes private hiking/X-Country skiing trails, open space with a lake, and Ausable River access.

Guest favourite
An open dining area features a long table adorned with a floral arrangement, surrounded by wooden chairs. A large stone fireplace is visible in the background, framed by bright yellow walls. Bar seating is provided at the kitchen counter, enhancing the communal space.
Home in Upper Jay
4.94 out of 5 average rating, 168 reviews

Parson Place

Custom-built home, added in 1994 to the original 1800s residence. Whiteface Mountain just 10 minutes away and Lake Placid is 25 minutes by car. Close to High Peaks Region. Large stocked kitchen, water filtration system, heated garage, elevator, fireplace, screened-in porch, jacuzzi (bath)tub, grill, basketball court, fire-pit - your Adirondack base camp!

Popular amenities for Upper Jay holiday rentals

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  3. New York
  4. Essex County
  5. Upper Jay