Upper Jay vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Upper Jay

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

0 of 0 items showing

1 of 3 pages

Top guest favorite

Cottage in Wilmington

5 out of 5 average rating, 105 reviews

ADK Cozy Mtn Cottage in Private Field-Dog Friendly

Newly constructed two-bedroom charming cottage in your own private field. Dog-friendly and a great place for the kids to play! Screened-in porch with ceiling fan for a peaceful nap, fire pit for some night-time stories under a wide-open night sky. Two TVs, wireless internet for a rainy day. Strawberry and blueberry beds right outside your front door! Cabin sleeps 4-Queen bed lower level - two twins in loft. With special arrangements a larger party could be accommodated in spacious field.

Top guest favorite

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

4.94 out of 5 average rating, 360 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 favorite

The exterior of the house showcases a wooden facade with large triangular windows, allowing natural light to illuminate the interior. Through the windows, a cozy seating area with a chair and a dog is visible, framed by falling snow and bare trees in the background.

Home in Keene

4.98 out of 5 average rating, 161 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 favorite

Chalet in Jay

4.95 out of 5 average rating, 217 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 favorite

A fire pit with flickering flames is set into a stone table, surrounded by lush greenery and hanging ferns. Planters with colorful flowers add to the vibrant atmosphere. The surrounding area offers a peaceful view of nature, providing a serene backdrop for relaxation.

Place to stay in Upper Jay

5 out of 5 average rating, 107 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.

Guest favorite

The loft sleeping area features natural wood paneling and exposed log beams. A soft grey bed occupies the space, complemented by a decorative pillow. A bedside table holds a lamp, and a small window provides a view of the outdoors, enhancing the cozy environment.

Tiny home in Wilmington

4.94 out of 5 average rating, 306 reviews

Tiny house in the Adirondacks!

This tiny house located in the Adirondacks in Wilmington, New York is cozy, cute and comfortable! It is convenient for many Adirondack activities including all types of biking, hiking, ,fishing, swimming, leaf peeping or just a quiet getaway. It is just minutes from Whiteface Mt. and a growing network of mountain bike trails. Ten miles to the beautiful village of Lake Placid .This tiny house is equipped with a kitchen, fire pit, and outdoor bathroom . Sleeps 3 adults comfortably.

Top guest favorite

A serene winter landscape showcases a brown cottage nestled among snow-covered trees. The mountains in the background are lightly dusted with snow, illuminated by the soft light of dawn. A tranquil river can be seen winding through the valley, framed by the vineyard in the foreground.

Cottage in Jay

4.96 out of 5 average rating, 115 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 favorite

The charming guesthouse is framed by snow-covered branches, showcasing twinkling outdoor lights that adorn the surrounding trees. A picnic table sits on a blanket of fresh snow, with wintery landscapes visible in the background. The inviting home features large windows and a welcoming porch.

Cabin in Upper Jay

4.96 out of 5 average rating, 312 reviews

Warner's Camp River House w/ Sauna & Swimming Hole

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 favorite

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, 480 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 favorite

A dining table is set with woven placemats, featuring a clear vase filled with vibrant yellow flowers. Large windows provide a view of a rustic barn and rolling green hills, framed by distant mountains under a clear sky.

Home in Wilmington

4.95 out of 5 average rating, 492 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 favorite

The kitchen area features a white counter island with two wooden stools. A modern black refrigerator stands alongside a wood-burning stove, with rustic log walls creating a cozy backdrop. Overhead lighting illuminates the space, while a clock is mounted on the wall for convenience.

Cabin in Jay

4.97 out of 5 average rating, 374 reviews

Adirondack Cozy Log Cabin

We are a pet friendly cozy cabin set in the Jay Range. This hand-crafted log cabin was built from the trees right on the property. Featuring authentic rustic charm along with all the modern conveniences, a new cook’s kitchen, dishwasher, gas range and a wood burning stove. Relax in the deep soaking tub, perfect for after a long hike in the high peaks district. If privacy, comfort and tranquility are what you are after, the Cabin is the right place for you.

Top guest favorite

A welcoming entryway is showcased, featuring a bench with decorative pillows. A light-colored wall is adorned with a 'WELCOME' sign, and several hooks are mounted for hanging items. A textured area rug lies over a patterned wooden floor, inviting guests in.

Apartment in Jay

5 out of 5 average rating, 144 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.