Book Luxury Holiday Rentals in Berkshire County

Award-winning homes from £98

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Home spotlights in Berkshire County

Summer Fridays

Summer Fridays

  • 10 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

A haven of tranquillity, this serene home is perfect for recharging your batteries. Step inside and be soothed by the classic Hamptons style – think ample-sized living spaces designed for entertaining, calm colours inspired by the coast and oodles of windows flooding each room with natural light.

Which Way The River

Which Way The River

  • 11 guests

  • 4 bedrooms

Shandaken, New York

Have you ever wanted your very own slice of the Catskills? Of course, you have.

The Masterplan

The Masterplan

  • 10 guests

  • 4 bedrooms

Tunkhannock Township, Monroe County

Just a two-hour drive from New York City, this home in the Poconos is more like a private resort, with an impressive list of amenities and all kinds of entertainment options for a large group. Set less than ten minutes away from scenic Lake Harmony by car, and close to various ski resorts like Jack Frost and Big Boulder Mountain, there are shops and restaurants within a few minutes drive, along with nearby golf courses and a water park.

The Berkshires Splendour

The Berkshires Splendour

  • 14 guests

  • 6 bedrooms

New Marlborough, Berkshire County

Nature meets luxury at this stunning Berkshire Mountain retreat. Just twenty minutes from Great Barrington and with hiking trails all around, this home is an idyllic escape from the hustle and bustle.


We selected the top 3% holiday homes in Berkshire County Holiday Rentals

Explore the 942 most perfect homes in our collection

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Most popular homes in Berkshire County

A Little Love Note

A Little Love Note

  • 6 guests

  • 2 bedrooms

New Lebanon, New York

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

The Edge

The Edge

  • 6 guests

  • 3 bedrooms

Ulster County, Rochester

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

Building Bridges

Building Bridges

  • 4 guests

  • 2 bedrooms

Astoria, Queens

Ode to the Past

Ode to the Past

  • 10 guests

  • 5 bedrooms

New Lebanon, New York

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Berkshire County. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Berkshire County has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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