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Home»Travel

Stay in castle used by Winston Churchill to plan D-Day with gothic clifftop views | UK | Travel

amedpostBy amedpostNovember 11, 2025 Travel No Comments3 Mins Read
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If you’ve been gawping at the dramatic scenery behind Alan Carr’s triumphant Traitors win and would love nothing more than to stay there then look no further.

With the game-show castle reserved for weddings – there is one striking and gothic alternative built by a famous American ex-owner, also once used by Winston Churchill to make WW2 battle plans.

Pennsylvania Castle may sound like a gimmick, but it does what it says on the tin.

Built by the founding father of Pennsylvania himself, this gorgeous and sprawling estate looks over rocky clifftops and due to a rare opening can be yours before Christmas. 

The gothic mansion has hosted a number of Royal weddings and was visited by the King and Queen’s to celebrate their wedding in 1800 on its completion.

The  sweeping sandy beach is just at your doorstep and is a short walk over the beautifully manicured lawn to the Jurassic Coast. There is an elegant reception room and room for two or three families to stay in one place. It is also a short distance from both Weymouth and Portland if you want to feel closer to some festive fun and fancy a long walk to a cosy pub.

The castle on Portland was built between 1797 and 1800 for John Penn, grandson of William Penn, the founder of Pennsylvania, after he was appointed Governor of the Isle of Portland and wanted a suitably grand coastal residence overlooking Church Ope Cove. 

Designed by leading architect James Wyatt, it’s is a prime showcase of late 18th Century Castelli’s Gothic – all turrets, battlements and romantic seaside drama rather than a true defensive fortress.  In the early 1800s the castle became quite fashionable and received occasional Royal visits during the Weymouth “sea-bathing” seasons, helping to put Portland on the map socially. 

Some say that D-Day invasion plans were hatched in the castle’s drawing room with Winston Churchill, General de Gaulle and General Eisenhower meeting to strategise on how to win the war, as per Project Gutenberg. The Pennsylvania Castle with the planning of the D-Day invasions were recognised with a grand ceremony on August 22, 1945, according to Elysian Estates.  The American ambassador John D. Winant opened a commemorative stone in its Victoria Gardens, celebrating  418,585 troops and nearly 144,093 army vehicles who passed by the spot a year ago.

Offered on an exclusive basis the grounds offers nine en-suite bedrooms sleeping up to 20 guests. Local restaurant, The Cove Inn is perfect for a relaxed evening meal with stunning views of the English channel. Their offering includes fresh seafood and crisp Dorset ales.

If you fancy an evening stroll you can choose one of the variety of cliff paths near Church Ope Cove or Chesil Beach, a name you may recognise from Ian McEwan’s book made into a screenplay starring Saorise Ronan.

For even better views of the sea, for the more adventurous you can climb the iconic Portland Bill Lighthouse for panoramic views of the coast, and walk along the clifftops to the Pulpit Rock.

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