Rent Luxury Accommodation in Winchelsea

We selected the 4988 homes worth renting in this location

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Home spotlights in Winchelsea

Woodland Reflections

Woodland Reflections

  • 2 guests

  • 1 bedrooms

Fairlight, Hastings

It's no wonder this glass-fronted eco-lodge squirrelled away in leafy protected woodlands has graced every high-end interior glossy going – and a few home design TV shows to boot. The ultimate year-round hideaway, here you'll swoon over the minimalist Scandi interiors, complete with a floating wood burner for winter nights and a pebble bath overlooking the forest for long soaks.

Beachfront Splendour

Beachfront Splendour

  • 16 guests

  • 8 bedrooms

Saint Leonards, East Sussex

This beautiful beachfront home is located in the popular seaside resort town of St Leonards in East Sussex. It’s close to sites of historical importance like Bodiam Castle and the ruins of Battle Abbey, but you may find yourselves entirely content to stay put – the beach is directly in front of the house, after all.

Shepherd's Cottage

Shepherd's Cottage

  • 2 guests

  • 1 bedrooms

Rolvenden, Cranbrook

With beautiful country views and a peaceful setting on the owners’ sheep farm, this perfectly petite home is the ideal base for exploring the Kentish Weald. You’re a ten-minute drive from the well-heeled town of Tenterden with its independent boutiques and tearooms as well as many National Trust properties.

The Dungeness Carriage

The Dungeness Carriage

  • 6 guests

  • 3 bedrooms

Lydd, Romney Marsh

This quirky home is full of charm and fascinating architectural design. A salvaged Victorian railway carriage has been incorporated into the design of the home, which boasts retro and urban styling – you’d never guess from the simple white cottage exterior.


We selected the top 3% holiday homes in Winchelsea Accommodation

Explore the 4988 most perfect homes in our collection

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Most popular homes in Winchelsea

Ready for a Close-Up

Ready for a Close-Up

  • 8 guests

  • 4 bedrooms

Broad Oak, Rye

Between Land and Sea

Between Land and Sea

  • 2 guests

  • 1 bedrooms

Rye, East Sussex

Barn To Be Wild

Barn To Be Wild

  • 8 guests

  • 4 bedrooms

Stone-cum-Ebony, Kent

A Good Apple

A Good Apple

  • 6 guests

  • 3 bedrooms

Whatlington, Battle

At The Waters Edge

At The Waters Edge

  • 15 guests

  • 6 bedrooms

Greatstone, Kent

Westside Cottage

Westside Cottage

  • 4 guests

  • 2 bedrooms

Lydd, Romney Marsh

Skylark's Song

Skylark's Song

  • 4 guests

  • 2 bedrooms

Guestling, Hastings

Camber Sands

Camber Sands

  • 12 guests

  • 5 bedrooms

Camber, Rye

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Frequently asked questions

Take a look at our exclusive collection of luxury Accommodation in Winchelsea, and find your dream home. Each and every listing on our site has passed a vigorous testing process with flying colours, which is why we can be so certain that our collection is the best of the best. Only 3% of homes will ever make it onto Plum Guide, emphasising our incredibly high standards and making your job as easy as possible. Every home comes fully furnished with a perfectly-equipped kitchen, essential bathroom toiletries, and all linen included, so you will find everything you need. Get in contact with our friendly team of experts, whose sole purpose is to find you your ideal home, and book your stay in the finest Winchelsea Accommodation for Rent.

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