Winchelsea Properties

We selected the 5012 homes worth renting in this location

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Home spotlights in Winchelsea

A Good Apple

A Good Apple

  • 6 guests

  • 3 bedrooms

Whatlington, Battle

Immersed in a 13-acre equestrian smallholding with horses, ducks and free-range chickens wandering the farmhouse garden, this cosy conversion is a picture of rural serenity. Whether you're curled up with a hot chocolate and a good book in hand by the wood-burning stove or are perched on a bench in the garden, you'll feel a world away from the fuss and flutter back home.

Pump It Up

Pump It Up

  • 6 guests

  • 2 bedrooms

Lydd, Romney Marsh

This striking holiday home was a pump station built during WWII to support the D-Day landings. Its conversion into a beach-side hideaway was so impressive that it was featured on George Clarke’s Remarkable Renovations, and it’s easy to see why.

Iron & Brick

Iron & Brick

  • 2 guests

  • 1 bedrooms

Hastings, East Sussex

Mouth-watering restaurants, cosy pubs and charming independent shops are all just moments away from this apartment nestled on the famous George Street in Hasting's Old Town. Step out the front door right onto the pretty pedestrianised lane and walk three minutes to the pebbled seafront, stopping for a coffee and a pastry along the way.

Vineyard Escape

Vineyard Escape

  • 4 guests

  • 2 bedrooms

Beckley, East Sussex

Wood-clad and terracotta-roofed, this idyllic little cottage is surrounded by fields and forest as far as the eye can see. Take in the countryside on a walk around the farm (with its own vineyard), meandering down to the river that runs through the grounds – and say hello to the owner’s two friendly Newfoundlands, who always love to welcome new guests.


We selected the top 3% holiday homes in Winchelsea Properties

Explore the 5012 most perfect homes in our collection

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Most popular homes in Winchelsea

Camber Sands

Camber Sands

  • 12 guests

  • 5 bedrooms

Camber, Rye

Beachfront Splendour

Beachfront Splendour

  • 16 guests

  • 8 bedrooms

Saint Leonards, East Sussex

The Writer's Cottage

The Writer's Cottage

  • 2 guests

  • 1 bedrooms

Sedlescombe, Battle

The Lofty Cow

The Lofty Cow

  • 2 guests

  • 1 bedrooms

Saint Leonards, East Sussex

The East Keeper's Cottage

The East Keeper's Cottage

  • 4 guests

  • 2 bedrooms

Lydd, Romney Marsh

Skylark's Song

Skylark's Song

  • 4 guests

  • 2 bedrooms

Guestling, Hastings

Ready for a Close-Up

Ready for a Close-Up

  • 8 guests

  • 4 bedrooms

Broad Oak, Rye

Thatcher in the Rye

Thatcher in the Rye

  • 4 guests

  • 2 bedrooms

Northiam, Rye

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Frequently asked questions

Plum guide offers a handpicked selection of the most luxurious properties in Winchelsea. Our homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book a short or extended stay and find your dream property in Winchelsea for a memorable holiday. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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