- Cotswold Festival of Steam – GWSR Cheltenham Racecourse Station – 24th-26th May
Get ready to embark on a journey through time, where the past comes alive and the heritage of steam locomotives is celebrated in all its glory. Join us for a long bank holiday weekend filled with the magic of steam, picturesque landscapes, and the rich history of the Cotswolds. The Cotswold Festival of Steam Gala is a spectacular event that brings together railway enthusiasts, families, and adventure seekers. Held amidst the charming Cotswold countryside, this gala showcases the elegance and power of steam locomotives, offering a unique experience for visitors of all ages. - Wychwood Festival – Cheltenham Racecourse – 30th May – 1st June
Wychwood, the unmissable family-friendly festival, returns in 2025. 3 days of Music, Comedy plus 100s of workshops and activities for all ages. Acts already announced include – Shed Seven, James, Doves, The Zutons, Daniel Bedingfield and Fisherman’s Friends. - Prescott Motorsport Festival – The Bugatti Owners’s Club, Prescott Hill – 7th – 8th June
Enjoy multiple disciplines of motorsport all in one place with our grass roots motorsport celebration weekend featuring Hill Climbing, AutoSOLO, Auto Test, Car Trials and Sporting Trials. - Cheltenham Science Festival – Imperial Gardens and various venues around the town – 3rd – 8th June
Asking the most important questions about the world today, Cheltenham Science Festival hosts six days of spectacular science. Bringing together the UK’s most respected scientists, favourite science communicators, writers, and artists to talk about today’s hottest topics. - By Royal Appointment – Everyman Theatre – 17th – 21st June
By Royal Appointment is a funny, poignant and celebratory new play about the kind of power that only a Queen can wield – she charms the world through coats and admonishes her family through a carefully chosen hat.
By Royal Appointment is a behind the scenes peek into the world of our most popular monarch and the image she presented to the world. Starring national treasure Anne Reid as The Queen, doyen of stage and screen Caroline Quentin as The Dresser, with Olivier award-winning James Dreyfus as The Milliner and Merchant Ivory and Poldark legendary James Wilby as The Designer. The new play is written by Daisy Goodwin who created the hit ITV series Victoria and directed by former Artistic Director of Shakespeare’s Globe, Dominic Dromgoole. - Cheltenham Food & Drink Festival – Montpellier Gardens – 20th – 22nd June
Cookery demonstrations, wine and cheese tastings. Artisan food producer stalls, fresh cuisine from a wide array of countries. Live music and entertainment. - Cheltenham Cricket Festival – Cheltenham College Cricket Pitch – Various dates 17th July and 5th August
Cheltenham Cricket Festival is believed to be the longest running cricket festival in the world and takes place in the iconic setting of Cheltenham College Cricket Pitch. The Festival programme includes a double header of both the men and womens’ county teams playing Sussex Sharks in the Vitality Blast. In the same tournament there is also a womens’ match versus Middlesex. There are County Championship matches against Lancashire and Middlesex and a One Day Cup match versus Derbyshire Falcons. - Cheltenham Literature Festival – Montpellier Gardent – 10th – 19th October
Cheltenham Literature Festival is the world’s longest-running literature Festival, leading the way in celebrating the written and spoken word, presenting the best new voices in fiction and poetry alongside literary greats and high-profile speakers. - October Showcase – Cheltenham Racecourse – 24th & 25th October
The Showcase raises the curtain to the 2025/26 Cheltenham season, once again, the thundering hooves, eager participants and excited fans will return to the Home of Jump Racing. - A Night at the Darts – The Centaur – Cheltenham Racecourse – Friday 28th November
This year’s event includes an unforgettable event featuring an all-star lineup, including world number one Luke Humphries and Stephen Bunting along with Rob Cross, Simon Whitlock and others! It’s set to be an epic head-to-head showdown you won’t want to miss.
Visiting one of these events? Get in touch to speak to one of our friendly team members to discuss our short term rentals in Cheltenham.