Holiday rentals in Upper Jay

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Top-rated holiday rentals in Upper Jay

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Top guest favourite
A warm-toned bedroom is highlighted by a wooden bed frame holding a spacious bed with a patterned blanket. Soft lighting from bedside lamps enhances the cozy atmosphere. Textured wall paneling and a green-framed window bring in natural light, complementing the inviting decor.
Cabin in Keene
4.92 out of 5 average rating, 207 reviews

Owl's Landing

Owl’s Landing Cottage is located high up in the foothills of the Sentential Mountain Range in scenic Keene NY, "Heart of the High Peaks." Keene is a major destination for hikers, climbers, skiers, anglers, artists and other adventurous and creative types. Trailheads and the East Branch Ausable River are easily accessible from the cottage. In Keene you’ll find locally-owned shops, markets, and cafes. We are 15 minutes from Whiteface Mountain, an Olympic Ski Resort and 15 minutes from Lake Placid.

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, 373 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, 199 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
4.96 out of 5 average rating, 249 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
Two red Adirondack chairs are positioned on a wooden terrace, overlooking a vast landscape of green trees and rolling mountains in the distance. A rustic wood table stands between the chairs, providing a natural focal point amidst the serene outdoor setting.
Guest suite in Elizabethtown
4.96 out of 5 average rating, 369 reviews

Adirondack Mountain View Retreat

30 minutes from Lake Placid, this unique mountain-view space features a comfortable, secluded 3-room guest suite opening out to a private covered terrace showcasing unmatched views of the Adirondack Peaks. A pet-friendly space ideal for outdoor enthusiasts, a couple's getaway, those working from home, or those just looking to have a peaceful retreat in the countryside - come enjoy our 25 acres of fields, forests, ponds and private riverbank. Also available: airbnb.com/h/adkretreat

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
4.97 out of 5 average rating, 145 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 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, 512 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!

Guest favourite
Home in Upper Jay
4.95 out of 5 average rating, 105 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, 145 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
Cabin in Upper Jay
4.95 out of 5 average rating, 339 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. Enjoy unmatched river views. The house is only 10 minutes away from Whiteface Ski Resort, 25 minutes from Lake Placid, and 5 minutes from Keene. Walk to a couple restaurants in Upper Jay. Recently featured in Travel + Leisure and Apartment Therapy.

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, fireplace, screened-in porch, Large jacuzzi (bathtub) Gas grill, Lighted basketball court, fire-pit - your Adirondack base camp!

Guest favourite
A cozy single-wide manufactured home is framed by lush greenery and tall trees, featuring a distinctive red metal roof. A grassy area enhances the inviting outdoor space, with scattered shrubs and plants contributing to a serene environment.
Home in Upper Jay
4.93 out of 5 average rating, 267 reviews

Running Brook

Located just 6 minutes from Whiteface Ski Center and 17 minutes from Lake Placid, this cozy 1.5 bedroom single wide manufactured home can comfortably sleep 3-4 people. This house is in close proximity to many activities that the area has to offer throughout the year, such as skiing, swimming, boating, hiking, and more!

Popular amenities for Upper Jay holiday rentals

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