Winchelsea Guest Houses

We selected the 5074 homes worth renting in this location

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Home spotlights in Winchelsea

Between Land and Sea

Between Land and Sea

  • 2 guests

  • 1 bedrooms

Rye, East Sussex

You’ll find this well-kept apartment in the heart of historic Rye, where cobbled lanes are flanked by medieval, half-timbered houses and hidden side streets give way to distant views across Rodney Marsh. You are mere footsteps from a number of traditional pubs, contemporary restaurants serving farm-to-table produce and just a ten-minute stroll to the Rye Castle Museum.

Beachfront Splendour

Beachfront Splendour

  • 16 guests

  • 8 bedrooms

Saint Leonards, East Sussex

This beautiful beachfront home is located in the popular seaside resort town of St Leonards in East Sussex. It’s close to sites of historical importance like Bodiam Castle and the ruins of Battle Abbey, but you may find yourselves entirely content to stay put – the beach is directly in front of the house, after all.

On My Radar

On My Radar

  • 2 guests

  • 1 bedrooms

Lydd, Romney Marsh

In its past life, this unique home used to be a research base for triangulated radar – now, it’s an acclaimed designer gem, perfect as a base for a romantic getaway. Situated near a functioning lighthouse, just steps away from the beach and surrounded by the Dungeness Nature Reserve, this place is a haven of peace and natural beauty.

Konik’s Rest

Konik’s Rest

  • 6 guests

  • 3 bedrooms

Benenden, Kent

If you like a bit of history with your holiday, look no further than this converted stable in the rolling hills of the Kent countryside. Step inside and you'll find hints of the building's past life in every room, coupled with some modern details like underfloor heating, a lavish soaker tub and fluffy bathrobes.


We selected the top 3% holiday homes in Winchelsea Guest Houses

Explore the 5074 most perfect homes in our collection

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Most popular homes in Winchelsea

Iron & Brick

Iron & Brick

  • 2 guests

  • 1 bedrooms

Hastings, East Sussex

Vineyard Escape

Vineyard Escape

  • 4 guests

  • 2 bedrooms

Beckley, East Sussex

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

The Writer's Cottage

The Writer's Cottage

  • 2 guests

  • 1 bedrooms

Sedlescombe, Battle

Sea Jet

Sea Jet

  • 10 guests

  • 5 bedrooms

Hastings, East Sussex

The Dungeness Carriage

The Dungeness Carriage

  • 6 guests

  • 3 bedrooms

Lydd, Romney Marsh

Skylark's Song

Skylark's Song

  • 4 guests

  • 2 bedrooms

Guestling, Hastings

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Frequently asked questions

Looking for guesthouse style accommodation in Winchelsea? You've come to the right place: Our homes come fully furnished with well-equipped kitchens, toiletries in bathrooms & all linen included. Book today and enjoy a short or extended stay in the best guesthouse style accommodation that Winchelsea has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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