Luxury October half term breaks

Golden woodland walks, homemade apple crumble and reading beside a crackling fire; our luxury October half term breaks invite families, large and small, to slow down and savour the season together. Discover our curated collection of private holiday cottages, exclusively yours, with many welcoming dogs too.

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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
    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 Up to 4 & Up to 2 guests
    Pets Sorry, no pets
    Features Outdoor infinity swimming pool, heated year round

    View More Details Save The Shearling

    Whether you're planning a multi-generational family gathering or an impromptu adventure with your nearest and dearest, our luxury October half term holiday cottages offer the space to truly switch off. These are homes with forest trails and coastal paths on their doorstep, where children can collect conkers whilst adults forage for chanterelles. Return from bracing walks to the warmth of a fire, gather for pumpkin gnocchi with browned butter prepared by a private chef, or slip into a heated pool as dusk settles.

    Our collection ranges from sprawling country houses in the Cotswolds with hot tubs and saunas, to seafront cottages in Cornwall and large Lake District retreats with acres of private fields and secret woodland to explore. However you choose to spend the October school holidays, each home offers the luxury of complete privacy, with every detail thoughtfully considered. If you're already dreaming ahead, discover our Luxury May half term breaks for springtime adventures across the UK and Ireland.

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