Luxury rentals in The Berkshires

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Top-rated luxury vacation rentals in The Berkshires

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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, 17 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 dining area is highlighted by a long wooden table surrounded by eight upholstered chairs. The space features a cozy fireplace with a decorative stone wall and a unique overhead light fixture. Large windows provide a view of the outdoors, enhancing the inviting ambiance.

Home in Catskill

4.96 out of 5 average rating, 28 reviews

Secluded modern home with private creek

Only 30 min to Hunter and Windham Mountains. Escape to a secluded modern three-bedroom retreat in the woods with soaring ceilings and expansive windows, set on ten acres of hilly, wooded forest, with private access to Kaaterskill Creek. The 12’ kitchen island and fully stocked chef’s kitchen are perfect for dinner parties. A 75” short-throw projector, Sonos sound system, and fiber internet for family movie night and any work you need to do from the private workspace.

Luxe

A modern living room features floor-to-ceiling windows offering a sunset view over rolling hills. Comfortable seating arrangements are present, alongside a geometric light fixture. Natural stone accents complement the space, enhancing the connection with the surrounding landscape.

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

An aerial view captures the modern retreat nestled among lush trees. Large windows reflect natural light, and a spacious deck is furnished with chairs. Surrounding green grass and flourishing gardens enhance the peaceful atmosphere, inviting guests to enjoy the serene outdoor setting.

Home in Kerhonkson

4.75 out of 5 average rating, 8 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!

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

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.