Rent Luxury Holiday Cottages in Winchelsea

We selected the 286 homes worth renting in this location

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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.

Cri de Coeur

Cri de Coeur

  • 2 guests

  • 3 bedrooms

Winchelsea, England

A quintessentially English countryside escape, you may have seen this characterful 16th-century manor feature in the film Mr Holmes and more notably in season three of The Crown. In honour of such a humble appearance – we've named this home after the episode in which it features, titled "Cri de Coeur".

Camber Sands

Camber Sands

  • 12 guests

  • 5 bedrooms

Camber, Rye

A stone’s throw from Camber Sands, this stylish home takes beach shack to glamorous new heights, making it the perfect coastal retreat for friendly get-togethers and extended families. The interior is characterfully designed using reclaimed and antique materials, offering a revitalised version of seaside chic.

Skylark's Song

Skylark's Song

  • 4 guests

  • 2 bedrooms

Guestling, Hastings

There's getting back to nature and then there's staying in this stunning 18th-century barn conversion, set on 350 acres of nature reserve. The house's location sounds like the start of a poem: next to a wildflower meadow and on the edge of a stream – beautiful.


We selected the top 3% holiday homes in Winchelsea Cottages

Explore the 286 most perfect homes in our collection

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Most popular homes in Winchelsea

Starry River

Starry River

  • 6 guests

  • 3 bedrooms

Camber, Rye

Vineyard Escape

Vineyard Escape

  • 4 guests

  • 2 bedrooms

Beckley, East Sussex

I See France

I See France

  • 6 guests

  • 3 bedrooms

Hastings, East Sussex

The Kingfisher

The Kingfisher

  • 6 guests

  • 3 bedrooms

Appledore Heath, Ashford

Marsh Marigold

Marsh Marigold

  • 4 guests

  • 2 bedrooms

Stone in Oxney, Tenterden

The Camber Dunes

The Camber Dunes

  • 6 guests

  • 3 bedrooms

Camber, Rye

Woodland Reflections

Woodland Reflections

  • 2 guests

  • 1 bedrooms

Fairlight, Hastings

On My Radar

On My Radar

  • 2 guests

  • 1 bedrooms

Lydd, Romney Marsh

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Frequently asked questions

Discover our curated collection of luxury holiday Cottages in Winchelsea. We painstakingly review all homes available in a destination and accept only the top 3% to ensure quality our guests can trust. Each of the Winchelsea Cottages in our collection comes fully furnished with essential bathroom toiletries, expertly-equipped kitchens and all linens included. Book your dream stay today and should you need some help, our friendly team of experts are on hand to help plan your perfect Cottage break.

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