Book a stay in one of the best homes in Winchelsea Beach

We selected the 5258 homes worth renting in this location

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Home spotlights in Winchelsea Beach

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.

The Friar's Eyrie

The Friar's Eyrie

  • 4 guests

  • 2 bedrooms

Winchelsea, England

A magical place to stay at any time of year, this elegant apartment sits within one wing of a vast Gothic mansion. Built in the early 19th Century, lovers of historical architecture will marvel at the ornate coving, the original fireplace and the stone mullion windows, and will find themselves staring out at a designated Site of Special Historic Interest – the imposing ruins of the 13th Century Franciscan abbey on the estate.

The Two Friars

The Two Friars

  • 8 guests

  • 4 bedrooms

Winchelsea, England

Two individual apartments in the guest wing of this stunning period building, these elegant homes can be rented together by larger groups or two families looking to escape to the Sussex coast together. In a spectacular setting, they're part of a Grade II Listed mansion that dates from 1819 and face the ivy-clad ruins of a 13th Century abbey.

Rye Retreat

Rye Retreat

  • 6 guests

  • 2 bedrooms

Udimore, East Sussex

Sea views and a hot tub — need we say more? This dog-friendly stone cottage was once part of the late comedian Spike Milligan’s home and, while it can be rented alongside the adjoining cottage for larger groups, we think it makes an ideal self-contained retreat.


We selected the top 3% holiday homes in Winchelsea Beach

Explore the 5258 most perfect homes in our collection

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Most popular homes in Winchelsea Beach

Camber Sands

Camber Sands

  • 12 guests

  • 5 bedrooms

Camber, Rye

Silver Skies

Silver Skies

  • 6 guests

  • 2 bedrooms

Udimore, East Sussex

Between Land and Sea

Between Land and Sea

  • 2 guests

  • 1 bedrooms

Rye, East Sussex

Rye Delight

Rye Delight

  • 2 guests

  • 1 bedrooms

Rye, East Sussex

Cri de Coeur

Cri de Coeur

  • 2 guests

  • 3 bedrooms

Winchelsea, England

Seaglass Loft

Seaglass Loft

  • 2 guests

  • 1 bedrooms

Rye, East Sussex

For A Moment

For A Moment

  • 6 guests

  • 3 bedrooms

Rye, East Sussex

Shell House

Shell House

  • 10 guests

  • 5 bedrooms

Camber, Rye

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