Your Perfect Stay

Discover Berkshire Rentals. A hand-curated portfolio of exquisite vacation homes across the world. Each property delivers the polished service of a luxury hotel paired with the privacy, space, and soul of a private residence. From the moment you book to the second you depart, every detail is handled so you can simply arrive and unwind.

  • Dates
    Whenever
  • Guests
    Whoever

Available Properties

Castle Townhouse
Great Barrington, MA

Castle Townhouse

8
3
Laurel Cottage
Great Barrington, MA

Laurel Cottage

6
3
Breezy Hill
Hillsdale, NY

Breezy Hill

9
4
White Birch
Great Barrington, MA

White Birch

14
4
Allen House with Pool
Stockbridge, MA

Allen House with Pool

16
7
Lake Garfield Waterfront
Monterey, MA

Lake Garfield Waterfront

8
3
Dixon Cottage
Sheffield, MA

Dixon Cottage

6
3
Lakeside Cottage
Egremont, MA

Lakeside Cottage

6
3
Hadley House
Stockbridge, MA

Hadley House

7
4
Sweetwater
Monterey, MA

Sweetwater

8
4
WanderWanderWander
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Curated Collection

Every home is personally vetted for exceptional design, prime location, and uncompromising comfort. We only list properties that meet our rigorous standards: stunning architecture, thoughtful furnishings, and unique character that make each stay feel bespoke rather than generic.

Effortless Service

24/7 concierge support, ultra-fast WiFi, private pools, gyms, and fully stocked kitchens come standard. Our team anticipates every need, whether it's arranging a private chef, securing last-minute reservations, or handling any request at 2 a.m., so you never lift a finger.

Inspiring Spaces

Wake up to jaw-dropping views, curated art, and serene interiors that refresh the soul. Each property is chosen for its breathtaking setting and meticulous details, turning every stay into a memorable escape where adventure, relaxation, and inspiration happen naturally.

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