Book Luxury Rental Apartments in Winchelsea

We selected the 3466 homes worth renting in this location

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Home spotlights in Winchelsea

The Two Friars

The Two Friars

  • 8 guests

  • 4 bedrooms

Winchelsea, England

Two individual apartments in the guest wing of this stunning period building, these elegant homes can be rented together by larger groups or two families looking to escape to the Sussex coast together. In a spectacular setting, they're part of a Grade II Listed mansion that dates from 1819 and face the ivy-clad ruins of a 13th Century abbey.

The Rose & Crown

The Rose & Crown

  • 2 guests

  • 1 bedrooms

Brenchley, Tonbridge

This charming cottage is on the edge of Matfield, a village with two pubs and a great setting-off point for countryside walks. This cosy abode is ideal for those wanting to explore the Kent and Sussex countryside, as well as the local wine farms.

Beachside Solitude

Beachside Solitude

  • 6 guests

  • 3 bedrooms

Sandgate, Kent

Beachfront living is hard to beat, and that's exactly what this fuss-free apartment offers. Set on Sandgate Esplanade, the shingled beach is just across the street.

Greenery & Lace

Greenery & Lace

  • 4 guests

  • 2 bedrooms

Fulham, London

Nestled in Fulham, this chic apartment has tranquillity and class running through its core. Suitable whether you’re in the city for business or leisure, you’ll even find an office here, making remote working for two people a breeze.


We selected the top 3% holiday homes in Winchelsea Apartments

Explore the 3466 most perfect homes in our collection

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Most popular homes in Winchelsea

The Cult of Beauty

The Cult of Beauty

  • 4 guests

  • 2 bedrooms

Deal, Kent

A Northerly Wind

A Northerly Wind

  • 2 guests

  • 1 bedrooms

Deal, Kent

Between Land and Sea

Between Land and Sea

  • 2 guests

  • 1 bedrooms

Rye, East Sussex

The Chalybeate Spring

The Chalybeate Spring

  • 6 guests

  • 2 bedrooms

Royal Tunbridge Wells, Tunbridge Wells

The White Horse

The White Horse

  • 2 guests

  • 1 bedrooms

Chalvington with Ripe, East Sussex

The Garden Ark

The Garden Ark

  • 3 guests

  • 1 bedrooms

Camden, London

Knightsbridge Red Brick

Knightsbridge Red Brick

  • 6 guests

  • 2 bedrooms

Chelsea, London

English Barleywine

English Barleywine

  • 4 guests

  • 2 bedrooms

Martin, Dover

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Frequently asked questions

There's no better place to book luxury Holiday Apartments in Winchelsea than our exclusive Plum Guide collection, which includes only the top 3% of homes. Every one of the homes on our site has been put through a painstaking vetting process with 150 checkpoints, culminating in a visit from a professional Home Critic. Every one of the remarkable homes on our books come fully furnished, with all linen and essential bathroom toiletries included, as well as a perfectly-equipped kitchen. Choose from one of the 3466 Apartments for Rent in our Winchelsea range, and discover the true meaning of luxury. Call on the help of our dedicated team too, to help make your choice as straightforward as possible.

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