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Thursday, February 12, 2026

“Explore the Historic Pennsylvania Castle for a Royal Stay”

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If you’ve been enchanted by the picturesque setting of the castle featured in Alan Carr’s recent Traitors win and wish to experience a similar stay in a castle, then your quest concludes here.

While the game-show castle is exclusively for weddings, an impressive gothic alternative with a fascinating history awaits. This castle, once owned by a prominent American figure and utilized by Winston Churchill for strategic planning during World War II, offers a compelling option.

Pennsylvania Castle may sound like a novelty, but it lives up to its promise. Originally built by the founder of Pennsylvania himself, this grand estate sits atop rugged cliffs and, with a rare opening, could be yours just in time for the festive season. Hosting several Royal weddings and graced by a visit from the King and Queen in 1800 to celebrate their nuptials, as per reports from the Express.

Situated just steps away from a sweeping sandy beach and a brief walk from the Jurassic Coast across a meticulously maintained lawn, this location is a dream. The property features an elegant reception room and ample space for multiple families to stay together. Additionally, it’s conveniently close to both Weymouth and Portland, ideal for those seeking a festive atmosphere and a cozy pub nearby.

Constructed between 1797 and 1800 for John Penn, the grandson of William Penn, the castle on Portland was erected following his appointment as Governor of the Isle of Portland, desiring a grand coastal residence overlooking Church Ope Cove.

Designed by the renowned architect James Wyatt, the castle stands as an impressive example of late 18th Century Gothic Revival, complete with turrets, battlements, and a romantic coastal grandeur, rather than serving as a functional military fortress.

In the early 1800s, the castle gained significant popularity, hosting occasional Royal visitors during Weymouth’s “sea-bathing” seasons, establishing Portland’s social standing.

Legend has it that the strategy for the D-Day invasion was formulated within the castle’s drawing room, where Winston Churchill, General de Gaulle, and General Eisenhower supposedly gathered to plan their path to victory, according to Project Gutenberg.

Pennsylvania Castle’s crucial role in the D-Day landings planning was commemorated with a grand ceremony on August 22, 1945, reported by Elysian Estates.

Exclusively available, the estate offers nine en-suite bedrooms accommodating up to 20 guests. The nearby dining venue, The Cove Inn, provides an ideal setting for a relaxed dinner with stunning views of the English Channel.

Their menu highlights fresh seafood and refreshing Dorset ales. For those interested in an evening stroll, numerous cliff-top trails near Church Ope Cove or Chesil Beach offer scenic views, a location recognizable from Ian McEwan’s book adapted into a movie featuring Saoirse Ronan.

For travelers seeking a more adventurous outing, ascending the iconic Portland Bill Lighthouse for panoramic coastal views and walking along the clifftops to Pulpit Rock for a superior sea view is recommended.

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