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Cozy cottage with pool, walking distance to lake

Cozy cottage with pool, fire-pit, and a short walk to the lake. Enjoy a relaxing stay at our home exploring the lake and local eateries, or a fun family getaway at the pool. Just a short drive to your winter fun at Jiminy Peak for skiing, or Saratoga during track Season. Minutes to the Crooked Lake House for your wedding stays. Don't forget your four legged family members, while you're snowshoeing, or swimming at the lake. With WIFI and A/C you can tele-work, while sitting pool side this summer.

Charming Guesthouse w/ Pool

Charming Guesthouse 20 Mins. from Saratoga Race Track — Pool, Fire Pit & Spacious Yard! Welcome to your perfect Upstate NY getaway - a cozy, private 1-bedroom guesthouse located on a half acre property in Clifton Park, just a quick drive from the world-famous Saratoga Race Track! Whether you're here for track season, concerts at SPAC, or simply to unwind, this peaceful retreat offers modern comforts, resort-style amenities, and a touch of country charm, complete with chickens and a spacious yard

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

You want to pop out of bed, walk downstairs and be right on the mountain - this is the place to be. This Stylish 1BR, 1BA suite with an additional Pull Out Queen sleeps 4 comfortably. It sits RIGHT in the Thatcher Building in front of the MAIN ski lift in Village Center. You can not get better than that! All the convenience without the bustle. This large 650 sq ft condo features brand new decor meticulously maintained, and includes a full kitchen with all the amenities. As a guest, you will

Comfortable Berkshires retreat on mtn resort, SISO

Once a retreat for an NYC real estate family, this grand yet comfortable place in Jiminy Peak has retained the feel of a chalet: perfect after a ski/hike/bike through the beautiful mountains around it. 4 bdrs allow your group to space out, and a great room with 20 foot high ceilings extends through the dining area. Convenient to many Berkshires spots (Tanglewood, museums, etc.), a 2nd living room, fireplace, jacuzzi, and access to slopes, hot tubs, heated pool & gym complete the perfect getaway.

Pool, Farmhouse, Pets Welcome at Roundhill Farm

An historic 1750 farmhouse on a quiet, beautiful 120 acre property. Huge rooms with wide plank original flooring, 6 bedrooms, large family room with fireplace, kitchen, dining room, and formal living room. The property includes a pond which you're welcome to skate on in the winter, and a horse barn and pastures. In the summer you'll have access to our in-ground pool. We welcome your pets! Come ski Jiminy Peak, only a 25-minute drive from this airbnb! The house sleeps 11 people comfortably.

"The Cabin" - Cozy & Rustic Home (Averill Park)

This luxurious log cabin, nestled on 200+ acres of private, expansive wilderness, is the perfect escape. Enjoy sunrise from the front porch, grill on the back deck and explore the 18-hole disc golf course, tranquil Japanese garden, croquet court, swimming pool and multiple walking trails throughout the forest property. Jiminy Peak Ski Resort, the Berkshires, and Saratoga Springs are all nearby. All amenities are provided with a personal touch that will make your stay relaxed and memorable.

Jiminy Peak Ski Loft with Hot Tub

This ski-in/ski-out loft at Jiminy Peak offers all of the amenities you could ever possibly ask for! A spacious 1 bedroom loft that sleeps up to 4 (1 Queen Bed, 1 Pullout Couch) is stylish and comfortable. We are the new owners and we are regularly updating the furniture and decor. A full kitchen, full bathroom with tub, ski locker / equipment storage, laundry in unit, dedicated parking spot, access to 2 pools and 2 hot tubs, a sauna, skiing, mountain cart, ropes course, and more!

Beautiful Jiminy Peak Townhome Family Friendly

Leave the city behind and come work remotely from our 3 bedroom, 2 bathroom newly renovated townhome. Whether you're visiting the Berkshires area in the winter for skiing at Jiminy Peak, or you're seeking summertime adventures on the lakes and the hiking trails, this 3 level home with puts you right in the middle of the action. Perfect for families, this rental is located in a community just a mile (3 minute drive) from the mountain and managed by Moresi Property Management.

Berkshire Getaway Ranch 3 acres + saltwater pool

Escape to the Berkshires in my cozy home sitting on 3 acres of land with in-ground saltwater pool. Enjoy the private, rural feel at this property with picturesque sunsets on the hills beyond. Under 5 min to Onota & Pontoosuc lakes, 15 min to Jiminy Peak & Bousquet ski resorts & a short drive to Lenox/Williamstown/North Adams. Light a fire in the living room & enjoy the ambiance of the vaulted wood ceilings & large picture windows framing views of the bucolic hills.

Bougie B’s Mountainside Getaway

Escape to our updated 2-bedroom, 2-bath condo at Jiminy Peak! Perfectly situated for the ski season, you'll enjoy quick access to both the slopes and apres ski. After a day on the trails, unwind at nearby restaurants like Christianson's Tavern or Bluebird & Co, offering top notch local eats. Bougie B's features updated amenities and that perfect touch of class to make you feel special. Come experience the beauty of the mountains today—your perfect escape awaits!

Private Estate • Pool • Pets • Nature Trails

Where Luxury Meets Nature on 130 Private Acres Escape to unmatched serenity at this custom-built villa nestled on a sprawling estate in Nassau, NY—just minutes from Kinderhook, Hudson, & Albany. With six bedrooms, three balconies, a gourmet kitchen, and expansive living spaces, this pet-friendly retreat offers the perfect blend of upscale comfort and natural beauty. Enjoy the private pool, scenic trails, and tranquil ponds—all wrapped in total seclusion.

Ski-InSki-Out Loft Lift&MT.Views

This ski-in, ski-out loft is located right at the base of the mountain in the Thatcher Lodge in the heart of the village at Jiminy Peak. Unmatched access to all of Jiminy Peak’s year-round activities. Skiing, mountain biking, hiking, tennis, swimming, fall foliage leaf peeping, shops, restaurants and the Mountain Adventure Park including the famous Mountain Coaster, Alpine Super Slide, Euro Bungy Trampoline, Soaring Eagle, Giant Swing, and climbing wall.