Book Luxury Vacation Rentals in Winchelsea

Award-winning homes from £98

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Home spotlights in Winchelsea

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.

Retro on the River

Retro on the River

  • 6 guests

  • 3 bedrooms

Rye, East Sussex

A breezy stroll from the town of Rye and a ten-minute drive from Camber Sands, this 70s-inspired home has been featured in magazines and on the BBC. The bedrooms are on the first floor, each boasting retro-style murals and vintage furniture.


We selected the top 3% holiday homes in Winchelsea Vacation Rentals

Explore the 5072 most perfect homes in our collection

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Most popular homes in Winchelsea

Cri de Coeur

Cri de Coeur

  • 2 guests

  • 3 bedrooms

Winchelsea, England

Between Land and Sea

Between Land and Sea

  • 2 guests

  • 1 bedrooms

Rye, East Sussex

Camber Sands

Camber Sands

  • 12 guests

  • 5 bedrooms

Camber, Rye

Ready for a Close-Up

Ready for a Close-Up

  • 8 guests

  • 4 bedrooms

Broad Oak, Rye

Starry River

Starry River

  • 6 guests

  • 3 bedrooms

Camber, Rye

The White Roses

The White Roses

  • 4 guests

  • 2 bedrooms

Wittersham, Kent

Do Not Disturb

Do Not Disturb

  • 2 guests

  • 1 bedrooms

Hastings, East Sussex

Skylark's Song

Skylark's Song

  • 4 guests

  • 2 bedrooms

Guestling, Hastings

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Frequently asked questions

Take a look at our collection of luxury Vacation Rentals in Winchelsea. All of the homes you'll find on Plum Guide come fully furnished with all linen, the best-equipped kitchens, and essential bathroom toiletries included. Each home is systematically reviewed before becoming part of our collection, so you can book your stay with total confidence. And if you require any assistance in finding the perfect Winchelsea Vacation Rentals for you, get in touch with our team of friendly experts, on hand to help with whatever you need.

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