Luxewoningen in Boys & Girls Club of the Berkshires Ice Rink

The Rye House: Paradise w/Pool+Hot Tub

Step into The Rye House, a captivating hillside oasis with 4 bedrooms and 2.5 baths, where every detail is designed to delight and highlight the natural beauty around you. Located just off Copake Lake, this property offers sweeping vistas of the rolling hillside—just 2.5 hrs from NYC! Outdoors, enjoy a pool, built-in hot tub, outdoor dining & lounging by the firepit, and an elevated deck. Inside, well designed interiors invite you to unwind while picture windows frame scenic views. Nearby Town

Lundy Estate: Farm, Yoga, Wedding, Sauna, Pool

Lundy Farm is a 62-acre estate and working farm located <2 hrs from NYC and surrounded by 30,000 acres of nature. The property sleeps up to 30ppl in 13 bedrooms with 13 dedicated bathrooms, and includes full access to the estate’s amenities; sauna, gym, commercial kitchen, yoga & meeting room, game room, pool, bikes, tennis, trails, fishing, and more. Your stay includes a full-service concierge to assist with private chefs, outdoor adventures, farm experiences, wellness, retreats, and weddings.

NEW Modern Cabin 8 mins from Skiing-Hot Tub & Gym

Immerse yourself in luxury at Timber Trail Lodge, an opulent 5-bedroom, 4 full bathroom estate nestled in Windham’s premier location. This expansive 4,000 ft² home offers the ultimate mountain escape, high-end amenities such as a modern spa, chef’s kitchen, Sonos, and an outdoor fire pit, perfect for entertaining. Adventure seekers can enjoy a private zip-line and proximity to Windham Mountain 8 minutes away. Timber Trail Lodge combines modern comfort, outdoor fun, and serene Mountain View’s

Casa Catskills: Luxury, Modern 9 Acre Escape

Escape to Casa Catskills, a modern, luxury mountain retreat on 9 private acres just 10 mins from Hunter & Windham Ski Resorts. The home’s amenities include a theater room, hot tub, sauna, pool table, multiple fireplaces, fully equipped kitchen with PFAS-free cookware and dedicated office space with beautiful mountain views. Enjoy 6 serene bedrooms (3 kings, 2 queens, 2 twins) and 5 spa-like bathrooms with radiant floors. Perfect for a wellness reset or city getaway. VIP services available.

Sunset Falls Estate, 167 Private Acres, Berkshires

A Berkshire private mountain estate in New Marlborough, MA 167 acres — home at 1,400 ft, summit at 1,640 Five ensuite bedrooms + the Bunk Room — sleeps 16 Indoor cedar spa room including cedar infrared sauna, cold plunge tub and steam room Expansive deck with hot tub, mountain views, lounging/dining Two wood-burning fireplaces, three fire pits, marked trails across the mountain Central to Great Barrington, Stockbridge, Litchfield County, Hudson Valley Concierge services available

Hudson Ridge | Hot Tub, Fire Pit & Fireplace

A stunning glass house with a breathtaking pool extending toward the Catskills. Set on 25 secluded acres in Hudson Valley, this architectural gem—featured in The New York Times—draws inspiration from Pierre Koenig’s Stahl House. Floor-to-ceiling glass surrounds two serene bedrooms, opening to a seasonal pool and year-round hot tub. Enjoy fast WiFi, two workstations, and total tranquility in this unique escape blending East Coast nature with West Coast charm.

Potter Mountain House: New Catskills Luxury Estate

Click: "Show more" to read full description. Stay in a newly restored 19th-century Greek Revival church in the high peaks of the Northern Catskills. Just 20 min to skiing at Windham Mountain! Potter Mountain House offers panoramic views from nearly every room with soaring ceilings, original wood beams, gas fireplace, chefs kitchen, office, a walk-in wine room and library within the steeple and four serene bedrooms and spa-like bathrooms.

Whimsy Woods - 14 Acre Millbrook Estate with Pool

Whimsy Woods, where contemporary design meets country escape, is a private getaway just minutes from the village of Millbrook. Approaching the property, you’ll feel the rich equestrian history of this historic hamlet, with paddocks and stables, sprawling meadows, and lush lawns. Through the wooden gate, find this uber-private 14-acre estate. The landscape features a mixture of manicured lawns and mature woodlands with walking trails.

Lux Mansion Windham: Hot Tub, Sauna, Mountain View

❆ Experience the ultimate retreat at Ulula Eco Resort, where luxury meets nature in the scenic Catskills. This 4770 sq ft chalet, made entirely of eco wood, features plush king-sized beds and a gourmet kitchen. Enjoy breathtaking views and top-notch amenities like a ground-level hot tub, sauna and cozy fire pit. Perfectly situated near Windham Ski Resort, it's the ideal base for skiing or serene mountain escapades.

Pinnacle Pointe | Year-Round Pool Spa Lake Theater

Escape to Pinnacle Pointe by Relaxtay — a stunning 9,500 sq ft mountain estate on 600 private acres, just 1.5 hours from NYC. In winter, enjoy a serene snow-covered retreat with panoramic mountain views, a year-round enclosed heated pool, private lake, sauna, gym, spa room, theater, bar, arcade, and chef’s kitchen. Sleeps large groups in luxe suites and bunk rooms. Private events are welcome with advance approval.

Historic Vanderbilt Estate Carriage House

This elegant, renovated carriage house is part of the former Vanderbilt Farm, a large model farm created by Frederick Vanderbilt as part of his vast Gilded Age estate. It was the first farm to bring fresh produce into New York City daily, on the railway owned by the Vanderbilt family. This carriage house is listed on the National Register of Historic Places jointly with a A McKim Mead & White designed farmhouse.

Riverside Hot Tub, Sauna & Resort Access

Riverside Hunter home with 6-person hot tub overlooking the water, Finnish cedar sauna, arcade game room, and wood-burning stove—1 minute from Hunter Mountain Resort entrance. Main Street restaurants and Fellows café are walkable, hiking trails under 5 minutes away. EV charger, fire pit, and waterfront setting with mountain views. Built for families and groups who want resort access with entertainment on-site.