KENTSTAYCATION
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© The Milkhouse
THE MILKHOUSE
THE DOG AT WINGHAM
Follow the suits of armour up the ancient staircase to one of the 12 beautifully designed rooms, each blending original period features with modern comforts. For a real taste of the past, book The Crimson Room, home to an ornate Tudor-style wooden four-poster bed said to have been used by Queen Elizabeth I as her retiring room during her visit to Cranbrook in 1573.
When you’ re ready to step outside, Cranbrook High Street has the town’ s history right on your doorstep. Nearby, St Dunstan’ s Church( stdunstanscranbrook. org. uk), heralding the‘ Cathedral of the Weald’, is well worth a visit, with its impressive 74-foot tower and open grounds leading into a peaceful recreational area for a long afternoon walk amongst the changing autumnal trees.
The Dog at Wingham, Canterbury thedog. co. uk
For a stay you’ ll want to return to time and time again, The Dog at Wingham combines an award-winning gastropub with eight luxury en-suite guest rooms, making it an ideal spot for an overnight escape in the Kent countryside. Each room is fitted with Hypnos beds, famously self-proclaimed as‘ the most comfortable beds in the world’, so a restful night is practically part of the package!
Wake up refreshed and ready for an equally special experience: the food. Holding two AA Rosettes and ranked No. 12 in the Estrella Damm Top 50 Gastropubs in 2026 under head chef Charlie Kendall- Smith, The Dog as its affectionately known, brings together a seasonal menu showcasing the best of Kentish produce.
On the à la carte menu, expect dishes such as Kentish lamb noisette served with crispy lamb belly, spiced carrots and glazed cabbage roll, alongside the classic Dog’ s Burger, made with dry-aged beef, treacle-cured bacon and a special house sauce. It is easy to admit that with food this good, The Dog would be worth the trip for dinner alone. Add a luxurious room, that Hypnos bed and a day out in the Kentish countryside, and you have all the ingredients for a pubcaytion definitely worth staying for.
The Milkhouse, Sissinghurst themilkhouse. co. uk
The perfect countryside bolthole, The Milkhouse combines clean, contemporary interiors with subtle nods to its historic surroundings. Inside, 16th-century timber beams and traditional Tudor brick fireplaces complement the four airy upstairs bedrooms, which are decorated in a soft, milky palette and finished with cosy furnishings. Expect crisp white linens, plush beds and original brickwork dotted throughout, creating a stay that feels both effortlessly stylish and wonderfully homely.
Downstairs, the restaurant and bar strike a balance between a relaxed village pub and a more refined dining space. Every dish is prepared and cooked on-site using local ingredients and the freshly made wood-fired pizzas easily take centre stage. From spicy salami to creamy goat’ s cheese, each one makes for a delicious lunch or dinner.
However, another draw of a stay at The Milkhouse is what lies just a 20-minute walk away: the acclaimed Sissinghurst Castle Garden( nationaltrust. org. uk). Steeped in history, the estate was once home to Vita Sackville-West and Harold Nicolson, who cultivated its grounds into the celebrated gardens they are today.
Come October, the gardens take on a distinctly autumnal character, with shades of crimson and terracotta sweeping across the grounds. For the best view, climb the 78 steps of the four-storey Elizabethan tower, where the panorama stretches beyond the gardens and across the Weald.
After all that exploring, finish off your visit at The Granary restaurant beside the gardens. The timber-framed restaurant makes an ideal stop for a warming coffee, or, better still, one of its indulgent hot chocolates piled high with whipped cream and marshmallows. The perfect sweet ending to an autumnal Kent staycation.
80 • www. insidekent. co. uk