Luxury cottages in Uppingham

Throughout the town, historic sandstone buildings house independent art galleries, antique shops and delis brimming with local cheeses and charcuterie, while family-run cafés serve specialty coffee alongside freshly baked pastries. On Fridays, the market square comes alive with stalls of local produce, a vibrant echo of Uppingham’s centuries-old trading tradition. The culinary scene is diverse: fine dining restaurants showcase Rutland’s seasonal ingredients and pair dishes with organic wines, while timber-framed pubs serve hearty, traditional fare.

Following the Uppingham Heritage Trail is a great way to experience the town’s historic sights in one route, including Uppingham School, the railway station and town hall. Beyond, the surrounding landscape is shaped for slow exploration. Rutland Water draws walkers, cyclists and sailors to its tranquil shores, and surrounding villages promise footpaths beneath wide skies. For a luxurious retreat in Uppingham, our collection includes a dog-friendly barn with far-reaching views, sumptuous modern interiors and a heated outdoor pool.