Luxury rentals in The Berkshires

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Top-rated luxury vacation rentals in The Berkshires

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Luxe

Home in Catskill

4.94 out of 5 average rating, 17 reviews

Cozy Winter Hideaway: Modern Cabin with Private Wo

Escape to a secluded modern three-bedroom retreat in the woods with soaring ceilings and expansive windows, with private patios for each bedroom. Set on ten acres of hilly, wooded forest, enjoy a picnic area and rock beach 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

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 Kerhonkson

4.17 out of 5 average rating, 6 reviews

A Retreat @ Hudson Woods With Main & Guest House

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!