Luxury rentals in The Berkshires

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Top-rated vacation rentals in The Berkshires

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Home in New Marlborough

Sunset Falls

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.

22–29 Nov

$4,686 SGD per night

Place to stay in Great Barrington

The Freeman Berkshires

Built in the 1800s, this Adirondack-style estate is set on 40 acres between New York and Boston in the Berkshires. Complete with a vineyard, games room, and private dock, there are plenty of ways to spend your days. If you’re up for adventure, there’s excellent skiing and hiking nearby. For a more relaxed getaway, sit and sip tea in the edible garden or catch up with a good book on the terrace. Copyright © Luxury Retreats. All rights reserved.

27 Sep – 4 Oct

$3,471 SGD per night

Home in Kerhonkson

A Retreat at Hudson Woods

Recently featured in Architectural Digest, this stylish retreat, nestled between the Catskills Mountains and the Hudson Valley, is the perfect escape for those looking to reconnect with nature. Spend your stay exploring the woods, relaxing by the pond, and enjoying food from the vegetable garden. Nearby, you’ll find breweries and fine dining in Kerhonkson. After a night out, the hot tub awaits. Copyright © Luxury Retreats. All rights reserved.

15–22 Apr

$2,447 SGD per night

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.

3–10 Jun

$3,333 SGD per night

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.

22–29 Mar

$6,776 SGD per night