Book Luxury Holiday Rentals in Benenden

Award-winning homes from £98

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Home spotlights in Benenden

Cottage of Wheelwrights

Cottage of Wheelwrights

  • 5 guests

  • 3 bedrooms

Staplecross, Robertsbridge

This charming cottage lies in the village of Staplecross, a wonderful mix of the modern and traditional. With a maximum occupancy of four adults, one child and one pet, this home is ideal for a lovely family stay.

The Friar's Monument

The Friar's Monument

  • 4 guests

  • 2 bedrooms

Winchelsea, England

As refined and attractive a home as you're likely to see, this single-storey apartment is a wing of a Grade II Gothic mansion. But what makes it truly unique is that it faces the ruins of an ancient Franciscan abbey that's of such historical importance it's been granted Scheduled Monument status.

Barn To Be Wild

Barn To Be Wild

  • 8 guests

  • 4 bedrooms

Stone-cum-Ebony, Kent

A perfect vacation spot for families—this home has an activity for everyone. Kids will love the in house game room with table tennis, foosball, and an Xbox for some friendly competition.

Shepherd's Cottage

Shepherd's Cottage

  • 2 guests

  • 1 bedrooms

Rolvenden, Cranbrook

With beautiful country views and a peaceful setting on the owners’ sheep farm, this perfectly petite home is the ideal base for exploring the Kentish Weald. You’re a ten-minute drive from the well-heeled town of Tenterden with its independent boutiques and tearooms as well as many National Trust properties.


We selected the top 3% holiday homes in Benenden Holiday Rentals

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Most popular homes in Benenden

Konik’s Rest

Konik’s Rest

  • 6 guests

  • 3 bedrooms

Benenden, Kent

The Writer's Cottage

The Writer's Cottage

  • 2 guests

  • 1 bedrooms

Sedlescombe, Battle

Vineyard Escape

Vineyard Escape

  • 4 guests

  • 2 bedrooms

Beckley, East Sussex

Camber Sands

Camber Sands

  • 12 guests

  • 5 bedrooms

Camber, Rye

The Rose & Crown

The Rose & Crown

  • 2 guests

  • 1 bedrooms

Brenchley, Tonbridge

Lazy Sunday Mornings

Lazy Sunday Mornings

  • 2 guests

  • 1 bedrooms

Biddenden, Kent

Quaystone

Quaystone

  • 4 guests

  • 2 bedrooms

Hawkhurst, Kent

Thatcher in the Rye

Thatcher in the Rye

  • 4 guests

  • 2 bedrooms

Northiam, Rye

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Benenden. 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 Benenden 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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