Berkshire County Romantic Accommodation

We selected the 942 homes worth renting in this location

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Age 13+

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Age 1 to 12

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Home spotlights in Berkshire County

River Song

River Song

  • 10 guests

  • 5 bedrooms

Dalton, Berkshire County

It’s no wonder why a multitude of actors, composers, and artists have hideaways in the Berkshires. This classic Berkshires home, originally built as a schoolhouse in 1866, is steeped in history and rural charm.

The Archway

The Archway

  • 9 guests

  • 4 bedrooms

West Hurley, Hurley

Urbanites looking for a tranquil getaway will enjoy the large indoor and outdoor spaces to relax and unwind. Each room has been lovingly styled by the host, Ayanna, who has instilled her character and charm into the home.

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.

Old Macdonald

Old Macdonald

  • 5 guests

  • 2 bedrooms

Stamford, New York

Once an 1890s carriage house, this home has been designed for country living for a small family. Low timber ceilings and hardwood floors retain the barn-like element, but instead of hay bales, you’ve got comfortable king-size beds for grown-ups and secret sleeping spots for kids in the mezzanine above the loft.


We selected the top 3% holiday homes in Berkshire County Romantic Accommodation

Explore the 942 most perfect homes in our collection

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Most popular homes in Berkshire County

Which Way The River

Which Way The River

  • 11 guests

  • 4 bedrooms

Shandaken, New York

Reynard's Den

Reynard's Den

  • 4 guests

  • 2 bedrooms

Liberty, New York

The Berkshires Splendour

The Berkshires Splendour

  • 14 guests

  • 6 bedrooms

New Marlborough, Berkshire County

A Little Love Note

A Little Love Note

  • 6 guests

  • 2 bedrooms

New Lebanon, New York

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

The Great Frontier

The Great Frontier

  • 4 guests

  • 1 bedrooms

Chatham, New York

Rise with the Sun

Rise with the Sun

  • 20 guests

  • 8 bedrooms

Pleasant Valley, New York

Art & Nature

Art & Nature

  • 6 guests

  • 4 bedrooms

Cragsmoor, Wawarsing

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Frequently asked questions

Discover the most romantic accommodation in Berkshire County. We’ve handpicked homes that are perfect for two, in soulful neighbourhood locations with characterful living spaces, sumptuous bedrooms and luxurious bathrooms. Book today and enjoy a short or extended stay in the most romantic accommodation that Berkshire County has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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