Luxury rentals in The Berkshires

The Rye House: Paradise w/Pool+Hot Tub

Step into The Rye House, a captivating hillside oasis with 3 bedrooms, a nursery, 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.

Home Sweet Hudson: A Retreat @ Hudson Woods

A Retreat @ Hudson Woods is a luxury oasis nestled in the private woods of Kerhonkson. Nearby breweries, farms, and fine dining restaurants make Kerhonkson a true destination, but the privacy and relaxing nature of A Retreat is a peaceful draw as well. Located on 8 acres of land in the Hudson Woods development, A Retreat was recently featured in Architectural Digest. There's also a brand new custom built cedar hot tub near the pool house! Please know pool umbrellas are currently unavailable!

Luxury 9 Acre Modern Catskills 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, pool table, indoor & outdoor 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.

Heated Pool! Sauna! Gym! Stunning Retreat + Views!

Skyline Ridge is a modern 4 bed, 4.5 bath getaway with breathtaking views, just under 3 hours from NYC. Chic and comfortable, it showcases sweeping vistas of the Hudson River and Catskill Mountains. Enjoy a prime location minutes from Hudson, plus a heated pool, hot tub, sauna, gym, fireplace, firepit, grill and laptop friendly workspaces. Nearby towns: Hudson (5mins), Catskill (10mins), Athens (10mins), Germantown (10mins), Saugerties (25mins), Woodstock (35mins)

Sunset Falls: A Berkshire Mountain Luxury Retreat

Welcome to Sunset Falls, where luxury meets nature in this modern architecturally significant home on 167 private acres. Open-concept living areas, floor-to-ceiling windows, and spacious great room. Breathtaking mountain views and full-service luxury amenities. Perfect for family gatherings and romantic getaways, this private oasis provides a serene escape, promising a unique, pampered experience with concierge service, ensuring a stay beyond the typical Airbnb.

Sunny Pond Estate | Private Pond, Gym, Sleeps 20

★ Recognized as one of our best. This home was a finalist in the 2025 AvantStay Awards, our annual celebration of top-tier stays. - Stunning, secluded estate located on a private swimming pond - Gourmet chef’s kitchen with top-of-the-line appliances - 9 bedrooms, three living areas, two dining areas, and a home office - Fully equipped gym with a Peloton - Movie room and playroom stocked with toys and games - Expansive yard boasting serene forest views

The Summit House | Best Views, Hot Tub, Game Rooms

One of a kind masterpiece perched above the clouds outside Windham. Experience complete privacy at this stunning all-season retreat, with unmatched mountain views and 6,500 sprawling sqft of space. With multiple lounges & bar areas, a bespoke game room, custom furnishings, and an outdoor area that is simply to die for, the Summit House is equally inviting for summer soirées and winter après. Why wait? Book your stay now.

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.

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.