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Book Luxury Short Stay Rentals in Winchelsea

We selected the 5064 homes worth renting in this location

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Home spotlights in Winchelsea

At The Waters Edge

At The Waters Edge

  • 15 guests

  • 6 bedrooms

Greatstone, Kent

Perched on the coast at Greatstone, this modern beach house makes for a luxurious family getaway. This contemporary home is designed with entertaining in mind – with plenty of open-plan communal spaces.

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.

The White Roses

The White Roses

  • 4 guests

  • 2 bedrooms

Wittersham, Kent

This cottage, set within a secluded location on the edge of Wittersham, is a serene retreat for a family gathering. The modern country-style interiors are inviting, while the ground-floor layout makes it accessible to all.

Starry River

Starry River

  • 6 guests

  • 3 bedrooms

Camber, Rye

Overlooking the river, this Camber cottage is ideally placed for a relaxing coastal retreat. It’s a short stroll down the lane to Broomhill Sands beach and just a little further along the coast to Rye – which has a wider selection of amenities.

We selected the top 3% holiday homes in Winchelsea Short Stay Rentals

Explore the 5064 most perfect homes in our collection

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Most popular homes in Winchelsea

Thatcher in the Rye

Thatcher in the Rye

  • 4 guests

  • 2 bedrooms

Northiam, Rye

Standen Farm Lower

Standen Farm Lower

  • 18 guests

  • 9 bedrooms

Benenden, Kent

English Barleywine

English Barleywine

  • 4 guests

  • 2 bedrooms

Martin, Dover

Shepherd's Cottage

Shepherd's Cottage

  • 2 guests

  • 1 bedrooms

Rolvenden, Cranbrook

I See France

I See France

  • 6 guests

  • 3 bedrooms

Hastings, East Sussex

Skylark's Song

Skylark's Song

  • 4 guests

  • 2 bedrooms

Guestling, Hastings

Gather & Grow

Gather & Grow

  • 12 guests

  • 6 bedrooms

Stone-cum-Ebony, Kent

Beachfront Splendour

Beachfront Splendour

  • 16 guests

  • 8 bedrooms

Saint Leonards, East Sussex

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Frequently asked questions

Browse our curated collection of Short Stay Rentals in Winchelsea. From impeccable interior design and chef-worthy kitchens, to fully furnished bathrooms and the inclusion of all linens, the homes in our collection come complete with everything you need. Each of the Winchelsea luxury short stay apartments in our collection has been expertly reviewed to ensure the quality standards you can trust, so book today to enjoy a getaway to remember. And should you need any assistance, our friendly team of experts are here to help you find the perfect home.

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