Luxury rentals in Western Massachusetts

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

Taghkanic House: Modern Oasis | Designer | Privacy

Taghkanic House is a modern Scandinavian inspired 5 bed, 3.5 bath retreat just 2 hours from NYC & minutes away from Taghkanic Lake for swimming & hiking. Set on 16 acres with sweeping views of the Catskills & designed with sustainability in mind, this eco-friendly home boasts rooftop solar panels, an EV charger, outdoor shower & large windows throughout that fill the space with natural light. Nearby towns: Hudson (20mins), Copake (20mins), Hillsdale (20mins), Catamount (30mins), Windham (45mins

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

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.

The Kemble Berkshires

Located in Lenox, one of Berkshire's most vibrant towns, this Gilded Age mansion is a beautiful event space with sweeping mountain views from the heart of the town. Your large group will appreciate the estate’s generous outdoor entertaining area, games rooms, and chef’s kitchen. In town, you’ll find delightful restaurants, bakeries, and antique shops. Copyright © Luxury Retreats. All rights reserved.

Pond, Gym & Movie Theater • Optional Guest House

★ Sunny Pond by AvantStay ★ - Stunning, secluded estate located on a private swimming pond - Fully equipped gym with a Peloton - Movie room and playroom stocked with toys and games - Gourmet chef’s kitchen with top-of-the-line appliances - 7 bedrooms, three living areas, two dining areas, and a home office - Expansive yard boasting serene forest views - 2 BR guest house available for an additional fee

Modern retreat, Catskill views from Pool & Hot Tub

The House on Slate Hill Road — a private 32-acre retreat with sweeping Catskills views, built for luxury group getaways, wellness weekends & milestone birthdays. Architect-designed with floor-to-ceiling windows, infinity pool (May–Nov) & year-round 7-person saltwater hot tub. Sleeps up to 14. 20 min from Hudson, 5 min to Chatham, ~2.5 hrs from NYC. Adults only.