Winchelsea Romantic Accommodation

We selected the 5582 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 Fossil Collector

The Fossil Collector

  • 4 guests

  • 2 bedrooms

Deal, Kent

Taking up the two floors of a Victorian townhouse, this home has a lovely view of Deal Castle out through the window. Inside, there's plenty to hold your attention, too.

The White Roses

The White Roses

  • 4 guests

  • 2 bedrooms

Wittersham, Kent

This cottage, set within a secluded location on the edge of Wittersham, is a serene retreat for a family gathering. The modern country-style interiors are inviting, while the ground-floor layout makes it accessible to all.

Do Not Disturb

Do Not Disturb

  • 2 guests

  • 1 bedrooms

Hastings, East Sussex

Set on the second floor of an apartment building overlooking Hastings' pedestrianised high street, this spot is right in the thick of the action. Lap up the atmosphere of the Old Town from the private balcony with a glass of wine in hand.


We selected the top 3% holiday homes in Winchelsea Romantic Accommodation

Explore the 5582 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

Shore Haven

Shore Haven

  • 6 guests

  • 3 bedrooms

Saint Leonards, East Sussex

Rye Retreat

Rye Retreat

  • 6 guests

  • 2 bedrooms

Udimore, East Sussex

The Friar's Eyrie

The Friar's Eyrie

  • 4 guests

  • 2 bedrooms

Winchelsea, England

Retro on the River

Retro on the River

  • 6 guests

  • 3 bedrooms

Rye, East Sussex

Quiet Countryside

Quiet Countryside

  • 4 guests

  • 1 bedrooms

Wittersham, Kent

Tenterden Charm

Tenterden Charm

  • 4 guests

  • 2 bedrooms

Tenterden, Kent

Ready for a Close-Up

Ready for a Close-Up

  • 8 guests

  • 4 bedrooms

Broad Oak, Rye

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Frequently asked questions

Discover the most romantic accommodation in Winchelsea. We’ve handpicked homes that are perfect for two, in soulful neighbourhood locations with characterful living spaces, sumptuous bedrooms and luxurious bathrooms. Book today and enjoy a short or extended stay in the most romantic accommodation that Winchelsea has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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