Book Luxury Short Stay Rentals in Winchelsea

We selected the 4988 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.

Westside Cottage

Westside Cottage

  • 4 guests

  • 2 bedrooms

Lydd, Romney Marsh

Situated on the southernmost point of Kent, this coastal cottage is an excellent choice for nature lovers – Dungeness Beach and Dungeness Bird Observatory are right on your doorstep. There’s an unfenced garden to the front of the home, and the rural location means phone reception can be variable – all the more reason to switch off, if you ask us.

Skylark's Song

Skylark's Song

  • 4 guests

  • 2 bedrooms

Guestling, Hastings

There's getting back to nature and then there's staying in this stunning 18th-century barn conversion, set on 350 acres of nature reserve. The house's location sounds like the start of a poem: next to a wildflower meadow and on the edge of a stream – beautiful.

Camber Sands

Camber Sands

  • 12 guests

  • 5 bedrooms

Camber, Rye

A stone’s throw from Camber Sands, this stylish home takes beach shack to glamorous new heights, making it the perfect coastal retreat for friendly get-togethers and extended families. The interior is characterfully designed using reclaimed and antique materials, offering a revitalised version of seaside chic.


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

Explore the 4988 most perfect homes in our collection

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Most popular homes in Winchelsea

Standen Farm Lower

Standen Farm Lower

  • 18 guests

  • 9 bedrooms

Benenden, Kent

On My Radar

On My Radar

  • 2 guests

  • 1 bedrooms

Lydd, Romney Marsh

Pump It Up

Pump It Up

  • 6 guests

  • 2 bedrooms

Lydd, Romney Marsh

Iron & Brick

Iron & Brick

  • 2 guests

  • 1 bedrooms

Hastings, East Sussex

Starry River

Starry River

  • 6 guests

  • 3 bedrooms

Camber, Rye

Do Not Disturb

Do Not Disturb

  • 2 guests

  • 1 bedrooms

Hastings, East Sussex

Gather & Grow

Gather & Grow

  • 12 guests

  • 6 bedrooms

Stone-cum-Ebony, Kent

Cottage of Wheelwrights

Cottage of Wheelwrights

  • 5 guests

  • 3 bedrooms

Staplecross, Robertsbridge

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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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