Rent Luxury Holiday Cottages in Winchelsea

We selected the 240 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Winchelsea

Golden Barley

Golden Barley

  • 2 guests

  • 1 bedrooms

Ashford, Kent

Right on the edge of Orlestone Forest and a twenty-minute drive from the coast, this quaint bolthole has been plucked from the lid of a chocolate box. Your host, Caroline, has created a cosy, clever and modern delight of a home with a mix of rustic and mid-century furnishings.

Bluebell Corner

Bluebell Corner

  • 8 guests

  • 4 bedrooms

Walmer, Kent

Located in the idyllic village of Kingsdown, this home offers up to eight guests the opportunity to escape to the Kentish coast for some well-deserved rest and relaxation. You couldn't be better placed for long walks along the shingle beach with your furry pal – best ended at the dog-friendly Zetland Arms.

A Cosy Cottage

A Cosy Cottage

  • 6 guests

  • 3 bedrooms

Burwash, East Sussex

This home is all about slowing down and switching off. Whether you’re sipping something refreshing in the lakeside garden or heading out to explore nearby walking trails and heritage sites, this is an easy-going base for a peaceful countryside break.

East Sussex Escape

East Sussex Escape

  • 6 guests

  • 3 bedrooms

Beckley, East Sussex

Surrounded by beautiful countryside – this cottage is nestled within the High Weald Area of Outstanding Natural Beauty. There are plenty of outdoor activities to enjoy in the area, including walking, hiking, and cycling.


We selected the top 3% holiday homes in Winchelsea Cottages

Explore the 240 most perfect homes in our collection

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Most popular homes in Winchelsea

Pump It Up

Pump It Up

  • 6 guests

  • 2 bedrooms

Lydd, Romney Marsh

Whitstable Oysters

Whitstable Oysters

  • 5 guests

  • 2 bedrooms

Whitstable, Kent

The River Runs By

The River Runs By

  • 4 guests

  • 2 bedrooms

Canterbury, Kent

His Majesty

His Majesty

  • 6 guests

  • 3 bedrooms

Kingsdown, Deal

Village Life

Village Life

  • 5 guests

  • 3 bedrooms

Newick, East Sussex

The Writer's Cottage

The Writer's Cottage

  • 2 guests

  • 1 bedrooms

Sedlescombe, Battle

The Grain Store

The Grain Store

  • 8 guests

  • 4 bedrooms

Lewes, East Sussex

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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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