Luxury rentals in The Berkshires

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Top-rated luxury vacation rentals in The Berkshires

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Luxe

A modern house with a Scandinavian design is nestled among tall grass and wildflowers. Large windows provide views of the surrounding landscape, while a sloped roof adds to the contemporary aesthetic. The structure is framed by lush greenery under a partly cloudy sky.

Home in Taghkanic

New place to stay

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

Luxe

A serene pool area is highlighted, featuring sun loungers positioned beside the water's edge. An umbrella offers shade, while expansive views of lush fields and rolling hills are visible in the background, creating a perfect setting for relaxation.

Home in Craryville

5 out of 5 average rating, 9 reviews

The Rye House: All-Season 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.

Luxe

An aerial view captures a stylish retreat surrounded by greenery, featuring a spacious swimming pool with sun loungers on the edge. The main house sits prominently, framed by trees and mountains in the background, complemented by a guest house nearby.

Home in Kerhonkson

4.4 out of 5 average rating, 10 reviews

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!

Luxe

Home in Hunter

5 out of 5 average rating, 7 reviews

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.

Luxe

A large, modern estate is displayed from a frontal viewpoint, featuring a mix of black and white siding. Solar panels are visible on the roof. Neatly trimmed shrubs line the property, and a wide porch extends across the front, providing ample outdoor space.

Home in South Cairo

5 out of 5 average rating, 29 reviews

Luna Cove: Premier Hudson Valley Getaway

Luna Cove is conveniently located between two iconic towns; Hudson, NY and Woodstock, NY. The estate offers many amenities for your leisure. You can enjoy private creek access, the pool, the hot tub, pickleball court, and barrel sauna! This property also offers a game room and a theater room along with a wellness spa. In addition to the main section of the home, there is a private wing with a separate external entrance featuring two bedrooms, a full bathroom, and its own kitchen area.

Luxe

A modern home with a wooden exterior is surrounded by green lawns and trees. A heated pool is seen in the foreground, accompanied by comfortable lounge chairs and a large umbrella for shade. The spacious deck is accessible from the house.

Home in Hudson

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)

Luxe

Home in New Marlborough

5 out of 5 average rating, 3 reviews

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.

Luxe

Home in Austerlitz

5 out of 5 average rating, 3 reviews

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

Luxe

Home in Millbrook

5 out of 5 average rating, 11 reviews

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.

Luxe

Chalet in Durham

5 out of 5 average rating, 4 reviews

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.

Luxe

An infinity pool is surrounded by well-maintained grassy areas and features a hot tub that complements the serene landscape. Several lounge chairs are positioned along the edge of the pool, offering a relaxing vantage point of the surrounding trees and meadows.

Place to stay in Hyde Park

5 out of 5 average rating, 3 reviews

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.

Luxe

Place to stay in Lenox

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.