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.

Add datesAdd guests / pets
    No destinations found
    2026

    View on map

    ( 1 )

    Filter results

    SORT BY

    PROPERTY TYPE

    POPULAR FEATURES

    OTHER FEATURES

    PRICE

    DISTANCE

    Fawn Wood

    Fawn Wood

    Hartfield, High Weald, East Sussex, UK

    With its own heated pool, Fawn Wood is a luxury retreat in High Weald that started life as a granary, hiding in a sylvan setting on the edge of the Ashdown Forest in East Sussex.

    Sleeps 6 (+2) guests
    Alternative Up to 4 guests
    Pets Two dogs are welcome
    Features Small-scale outdoor heated pool (available May - September inclusive), professional Trackman golf simulator and SimWay Hunt Pro shooting simulator (advance booking required, incurs an additional cost), Big Green Egg barbeque and outdoor pizza oven.

    View More Details Save Fawn Wood

    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.

    Not quite what you're looking for?

    Find more properties:

    Alternative Collections

    1 properties
    view on map