Holiday rentals in Upper Jay

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Top-rated holiday rentals in Upper Jay

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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, 303 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 in Upper Jay
4.95 out of 5 average rating, 370 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, 190 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, 242 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
Place to stay in Upper Jay
5 out of 5 average rating, 129 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. This rental offers all the modern conveniences plus old world charm. 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.

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, 318 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
The image showcases a serene landscape featuring a rustic cottage framed by trees displaying autumn foliage. The sun rises gently behind the distant mountains, casting a soft glow over the property and highlighting the peaceful Ausable River. A fence delineates the grassy area, enhancing the tranquil ambiance.
Cottage in Jay
4.96 out of 5 average rating, 141 reviews

The Covered Bridge Cottage- Ausable Riverfront

Situated directly by the Ausable River and surrounded by beautiful vineyards and gardens you will be immersed in nature at any time if the year. It's sure to restore the soul. The gentle rumble of the river is ever present as you look out over the natural beauty. During the summer cool off in the river and come back to the screened in porch for an evening meal. In the winter fire up the pellet stove and get cozy. 15 minutes to Whiteface and Keene and 25 Minutes to Lake Placid.

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, 513 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
Cabin in Upper Jay
4.99 out of 5 average rating, 101 reviews

The Log Cabin near Whiteface, Hot Tub & Sauna

Perfect for couples & large groups! Cozy cabin + optional outbuildings. 10 minutes to the ski resort, on-site swimming hole & fishing access, cedar hot tub & sauna, foosball, hiking, walkable dining, boutique furnishings. The Log Cabin at Warner’s Camp is a piece of art. This property consists of a bespoke 3 bed, 2 bath log cabin, a studio cabin with additional bed and bath, plus an extra sleeper cabin (a charming enclosed lean-to, overlooking a stream).

Top guest favourite
The living room features a television on a console, surrounded by two armchairs and a coffee table. Natural light fills the space through sliding glass doors, which lead to a private back deck. A patterned area rug adds texture to the flooring.
Flat in Jay
5 out of 5 average rating, 160 reviews

Newly renovated one bedroom apartment in Adk mtns

Queen-sized bed in bedroom and queen-sized sofa bed in living room. Two Smart TVs with streaming capability and guest Wi-Fi. Brand new furniture, flooring and bath. Newly updated, fully-equipped kitchen with coffee bar. Separate entrance off heated enclosed foyer. Private back deck with beautiful backyard views. Close to Whiteface Mountain and Lake Placid. Nearby to beautiful hiking trails in the famous Adirondack Mountains and Adirondack Lakes.

Superhost
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.

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

  1. Airbnb
  2. United States
  3. New York
  4. Essex County
  5. Upper Jay