Luxury cottages in Oakham

In England's smallest county, this characterful market town sits pretty. Here, cobbled lanes lead to independent delis, and traders spill across historic squares. Its namesake castle,14th-century church and surrounding verdant pastures create an idyllic backdrop for a stay in one of our luxury cottages in Oakham.

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    Dragonwood Boat House

    Dragonwood Boat House

    Oakham, Rutland, UK

    A unique, romantic space Dragonwood Boat House is a traditional Victorian home with an Italian twist, sitting pretty on the water near Oakham in Rutland.

    Sleeps: Up to 2 guests
    From: £1,295 per week, £995 per short break
    Pets: Sorry, no pets
    Features: Kayaks, well-stocked fishing lakes

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    The Shearling

    The Shearling

    Uppingham, Rutland, UK

    Time at this secluded Rutland retreat unfolds at a gentler pace. Find calm in the tranquil interiors, beautifully designed garden and heated infinity pool with pastoral views.

    Sleeps: Up to 6 guests
    Alternative Group Option: Up to 4 & Up to 2 guests
    From: £2,995 per week, £2,250 per short break
    Pets: Sorry, no pets
    Features: Outdoor infinity swimming pool, heated year round

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    For those drawn to country charm on a quieter stage than the Cotswolds or Somerset, Rutland’s motto – multum in parvo – ‘much in little’ delivers on its promise in Oakham. Its historic marketplace, framed by honey-hued Georgian architecture, shelters artisanal delis, independent bookshops and twice-weekly markets to stir the senses with local, seasonal produce. Michelin-recognised restaurants sit alongside organic wine bars and pubs serving chilled pints of regional bitter and the county's own Rutland Pippin – a pork pie shaped like an apple.

     At the town's ancient heart stands Oakham Castle, a masterpiece of Norman architecture where the ancient ritual of horseshoe tributes has been upheld for centuries. Further afield, Rutland Water, Britain's largest reservoir, draws sailors and birdwatchers seeking ospreys and red kites. Cycle the 25-mile perimeter through woodlands and quiet coves or windsurf and fish its shimmering waters. For a romantic escape in Oakham, our collection includes a lakeside Victorian boathouse with sprawling private waters and extensive gardens.

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