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, 14 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

The spacious property showcases lush greenery and a variety of amenities, including an in-ground pool and a private pickleball court. Surrounding areas are landscaped, providing a serene outdoor setting ideal for relaxation and recreation. The house is set against a backdrop of rolling hills.

Home in Hurley

4.94 out of 5 average rating, 16 reviews

Family Manor Sleeps 18 w Pickleball, Pool, HT, FP

Welcome to Fox Hill, a Family Manor equipped to entertain up to 18 people with endless amenities both inside & out. This spectacular property is managed by Root & Ramble. The home has 8 bedrooms, 2 private rooms with sofa beds, 4.5 bathrooms, game room, bright and spacious chef's kitchen and amenities galore both inside & out. Note: this property recently switched to new management. The home has 37 5-star reviews under the old listing. Also check out our Superhost reviews!

Luxe

The modern retreat is set among trees with a combination of wooden and sleek black exterior. A spacious concrete patio extends in front, with outdoor seating visible. Natural stone paths lead up to the entrance, blending harmoniously with the surrounding forest landscape.

Home in Catskill

4.96 out of 5 average rating, 25 reviews

Escape To The Woods, Light-Filled Modern Home

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 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

4.71 out of 5 average rating, 7 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!