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

    ( 4 )

    Filter results

    SORT BY

    PROPERTY TYPE

    POPULAR FEATURES

    OTHER FEATURES

    PRICE

    DISTANCE

    Tilda

    Tilda

    Fordingbridge, New Forest, Hampshire, UK

    Woodland hideaway meets minimalist design at Tilda. Here, the gentle trickle of the River Allen and splash of jumping blue trout wash away any remnants of city living.

    Sleeps Up to 2 guests
    Pets One dog is very welcome, two well-behaved dogs on request.
    Features Hot tub and fire pit

    View More Details Save Tilda

    The Sanctuary

    The Sanctuary

    Lymington, New Forest, Hampshire, UK

    Bordering the New Forest in Hampshire's Lymore Valley, The Sanctuary is an industrial luxury cabin with a hot tub, fire pit, and a pair of cruiser bikes for peddling to the beach.

    Sleeps Up to 2 guests (+1)
    Pets Two well-behaved dogs are welcome
    Features Sauna, Jacuzzi hot tub, Kadai fire pit and cruiser bikes

    View More Details Save The Sanctuary

    Pepper Shack

    Pepper Shack

    Lymington, New Forest, Hampshire, UK

    A luxury cabin that feels like a winter cave, Pepper Shack is a moody home with a hot tub, pizza oven, and couples' bikes, made for romantic stays near the New Forest in Hampshire.

    Sleeps Up to 2 guests (+1)
    Pets Two well-behaved dogs are welcome
    Features Sauna, hot tub, Kadai fire pit, outdoor pizza oven and two cruiser bikes

    View More Details Save Pepper Shack

    Forestkeepers

    Forestkeepers

    Fordingbridge, New Forest, Hampshire, UK

    A bespoke treehouse, zip-wire, and outdoor pool await at Forestkeepers, where a garden gate leads straight into Hampshire's New Forest, tempting picnics in woodland glades.

    Sleeps Up to 12 guests (8 adults and 4 children)
    Alternative Up to 6 guests
    Pets Two well-behaved dogs are welcome, or three on prior request
    Features Heated outdoor swimming pool heated April - October inclusive), treehouse, zipwire, trampoline, football goals, netball hoop, games room with air hockey and arcade machine, cinema room

    View More Details Save Forestkeepers

    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

    4 properties
    view on map