Luxury May half term breaks

May marks the turning point when spring gives way to summer across the UK and Ireland. Later sunsets bring longer days, whilst the countryside erupts into colour and birdsong. Our luxury May half term breaks are designed for making the most of precious family time.

Add datesAdd guests / pets
    No destinations found
    2026

    View on map

    ( 9 )

    Filter results

    SORT BY

    PROPERTY TYPE

    POPULAR FEATURES

    OTHER FEATURES

    PRICE

    DISTANCE

    The Studio

    The Studio

    Upper Slaughter, Gloucestershire, The Cotswolds, UK

    In the heart of Upper Slaughter, one of England’s “doubly-thankful” villages, The Studio is a luxury Cotswolds barn that wouldn’t be out of place in New York's artsy Tribeca.

    Sleeps: Up to 2 guests
    Pets: Sorry, no pets
    Features: Pizza oven, fire pits and 2-night stays available

    View More Details Save The Studio

    Four Hundred Summers

    Four Hundred Summers

    Ablington, Bibury, Gloucestershire, The Cotswolds, UK

    With an ashlar chimney that sends smoke signals curling above the gable roof, Four Hundred Summer is a luxury Cotswolds cottage with a hot tub that brings Nordic clout to Ablington.

    Sleeps: Up to 2 guests
    Pets: Sorry, no pets
    Features: Wood-fired hot tub

    View More Details Save Four Hundred Summers

    The Flower Press

    The Flower Press

    Bibury, Gloucestershire, The Cotswolds, UK

    Emerald green in spring, fire red in autumn; luxury cottage The Flower Press is a French countryside-inspired home and garden in the quintessentially Cotswolds village of Bibury.

    Sleeps: Up to 4 guests
    Alternative Group Option: Up to 2 guests
    Pets: Two well-behaved dogs of small or medium sized breeds over the age of 12 months are welcome

    View More Details Save The Flower Press

    The Find

    The Find

    Cranham, Cheltenham, Gloucestershire, The Cotswolds, UK

    A dynamic pairing of luxury Cotswolds homes in Cranham, The Find is an old stone cottage and architect-designed glass extension in a beautifully secluded valley near Cheltenham.

    Sleeps: Up to 12 guests
    Pets: Two dogs are welcome
    Features: Trampoline, hot tub hire is available (please enquire for details)

    View More Details Save The Find

    Saxon

    Saxon

    Maugersbury, Stow-on-the-Wold, Gloucestershire, The Cotswolds, UK

    Over a thousand years of history have unfolded between the walls of this elegant manor. Today, Saxon offers a serene escape near Stow-on-the-Wold in the Cotswolds.

    Sleeps: Up to 12 guests
    Pets: One small to medium dog is welcome
    Features: Hot tub, cinema snug with projector and games room

    View More Details Save Saxon

    Gulliver´s Hall

    Gulliver´s Hall

    Bisley, Stroud, Gloucestershire, The Cotswolds, UK

    A playful Cotswolds farmhouse with all the frills of a luxury country house; Gulliver's Hall is a unique family home in the beating heart of the Cotswolds, complete with a heated pool, sauna, hot tub and padel court.

    Sleeps: Up to 21 guests
    Alternative Group Option: Up to 15 guests
    Pets: Two well-behaved dogs are welcome on prior request
    Features: Outdoor heated pool (Apr-Oct), spa bath, sauna, steam room, outdoor kitchen (pizza oven, paella burner), games/cinema room, padel court, croquet lawn and gym (spring ´26). Please enquire for further details.

    View More Details Save Gulliver´s Hall

    Anthology Farm

    Anthology Farm

    Cheltenham, Gloucestershire, The Cotswolds, UK

    With an indoor pool, tennis court, and yoga studio, members-only health club Anthology Farm is a luxury country estate made for family gatherings near Cheltenham in the Cotswolds.

    Sleeps: Up to 18 guests (increasing to 22 from May 2026)
    Alternative Group Option: Up to 18 & Up to 10 guests
    Pets: Pets are considered on prior agreement
    Features: Heated indoor swimming pool, cinema room, tennis court, table tennis, gym equipment, purpose built yoga studio and electric car charging point. From May 2026 there will also be a sauna, ice bath and two treatment rooms.

    View More Details Save Anthology Farm

    Weddings at Gulliver´s Hall

    Weddings at Gulliver´s Hall

    Bisley, Stroud, Gloucestershire, The Cotswolds, UK

    Modern bohemians, lovestruck eccentrics, and pairs of playful classicists, meet Gulliver’s Hall: a made-to-measure luxury wedding venue available for exclusive hire in the Cotswolds.

    Sleeps: Up to 21 guests
    Alternative Group Option: Up to 70 & Up to 40 guests
    Pets: Two well-behaved dogs are welcome on prior request
    Features: Outdoor heated pool (Apr-Oct), spa bath, sauna, steam room, outdoor kitchen (pizza oven, paella burner), games/cinema room, tennis court (until Oct ´25), croquet lawn, padel court and gym (spring ´26). Please enquire for further details.

    View More Details Save Weddings at Gulliver´s Hall

    Weddings at Anthology Farm

    Weddings at Anthology Farm

    Cheltenham, Gloucestershire, The Cotswolds, UK

    An 18th century barn designed with love-filled celebrations and grand gatherings in mind, Anthology Farm is nestled in an ancient Cotswolds valley on the outskirts of Cheltenham. A venue as idyllic for summer marquee weddings as winter celebrations.

    Sleeps: Up to 18 guests (increasing to 22 from May 2026)
    Alternative Group Option: Up to 60 & Up to 30 guests
    Pets: Pets are considered on prior agreement
    Features: Wedding barn, heated indoor swimming pool, tennis court and electric car charging point

    View More Details Save Weddings at Anthology Farm

    With the May half term just around the corner, generously parcelled up with the second May Bank Holiday, there’s no better time to stay on our wild isles. May's temperate warmth brings with it the first real taste of summer, from the gorse-tangled paths that border the Cornish coastline to the rugged Welsh peaks. Perhaps you'll take a stroll through sun-dappled ancient woodland, enjoy an invigorating cold-water swim, or find creative nourishment in a nearby market town. Whether you're planning a family adventure for the full holiday or an impromptu gathering of friends, our luxury May half term stays provide opportunity for restoration and adventure alike.

    Some homes are simply made for school holidays: places where children can freely play in rambling secret gardens whilst the adults lounge on an al fresco terrace – wrapped in blankets around a fire pit as the evening cools. From a Cotswolds farm stay with facilities to rival any luxury spa to a remote mountain hideaway in Ireland, our collection invites every kind of escape. As the evenings lengthen, gather for wood-fired pizzas and ribboned courgette salad crafted by a private chef or take a twilight dip in an infinity pool as the landscape dissolves into the horizon. Whatever an ideal half term looks like for you, our collection promises blissful respite for all ages.

    Not quite what you're looking for?

    Find more properties:

    Alternative Collections

    9 properties
    view on map