Book Luxury Holiday Rentals in Winchelsea

Award-winning homes from £98

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Home spotlights in Winchelsea

Vineyard Escape

Vineyard Escape

  • 4 guests

  • 2 bedrooms

Beckley, East Sussex

Wood-clad and terracotta-roofed, this idyllic little cottage is surrounded by fields and forest as far as the eye can see. Take in the countryside on a walk around the farm (with its own vineyard), meandering down to the river that runs through the grounds – and say hello to the owner’s two friendly Newfoundlands, who always love to welcome new guests.

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.

Song to the Sea

Song to the Sea

  • 14 guests

  • 6 bedrooms

Saint Leonards, East Sussex

From its enviable spot in St Leonards-on-Sea, this former hotel has been transformed into a contemporary coastal retreat. Featuring a private roof top terrace and a large deck area with a hot tub, this is the perfect setting to slow down and savour quality time together.

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".


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

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Most popular homes in Winchelsea

The Two Friars

The Two Friars

  • 8 guests

  • 4 bedrooms

Winchelsea, England

The Camber Dunes

The Camber Dunes

  • 6 guests

  • 3 bedrooms

Camber, Rye

The Kingfisher

The Kingfisher

  • 6 guests

  • 3 bedrooms

Appledore Heath, Ashford

The Writer's Cottage

The Writer's Cottage

  • 2 guests

  • 1 bedrooms

Sedlescombe, Battle

The Fog Signalling Building

The Fog Signalling Building

  • 2 guests

  • 1 bedrooms

Lydd, Romney Marsh

Retro on the River

Retro on the River

  • 6 guests

  • 3 bedrooms

Rye, East Sussex

On The Sands

On The Sands

  • 10 guests

  • 5 bedrooms

Camber, Rye

Woodland Reflections

Woodland Reflections

  • 2 guests

  • 1 bedrooms

Fairlight, Hastings

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Winchelsea. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Winchelsea has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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