- Cheltenham Festival – Cheltenham Racecourse – 11th – 14th March
Cheltenham Festival 2025 is the pinnacle event of the jump-racing calendar. Guaranteed excellence, whether you join on Champion Day on Tuesday, Style Wednesday, St Patrick’s Day on Thursday or Gold Cup Day on Friday. - The Craft Festival – Cheltenham Town Hall – 21st – 23rd March
Craft Festival Cheltenham returns with a hundred of the finest designer makers from across the UK exhibiting at Cheltenham Town Hall. Buy directly from designer makers of jewellery, ceramics, furniture, textile artists, glass and many more. - Cheltenham Town FC vs Milton Keynes Dons – EV Charger Points Stadium – Saturday 22nd March at 3pm
Cheltenham Town will be looking to secure a home win as MK Dons have been struggling for results in recent weeks. - Fresh: Art Fair – The Centaur, Cheltenham Racecourse – 3rd – 6th April
Fresh: Art Fair Cheltenham will host over 40 leading galleries showing 4000 artworks by 400 artists from across the UK and beyond. Browse and buy original prints and paintings, sculpture, glass and ceramics from as little as £50 to £20,000 or more, but most within your budget. - Cheltenham Town FC vs Doncaster Rovers – EV Charger Points Stadium – Saturday 5th April
Cheltenham look to face a stiff challenge against promotion chasing Doncaster Rovers. - Roald Dahl’s Charlie and the Chocolate Factory – Everyman Theatre – 15th – 19th April
A performance by Cheltenham Operatic and Dramatic Society. Escape into a world of pure imagination this Easter with this devilishly delicious story of young Charlie Bucket. Based on the iconic story from Roald Dahl, join Charlie and Grandpa Joe as they enter the iconic world of Willy Wonka and his incredible chocolate factory. - The April Meeting – Cheltenham Racecourse – 16th and 17th April
The April Meeting is a wonderful two-day meeting at the Home of Jump Racing. The Spring sunshine shining over the famous Cleeve Hill and hallowed Cheltenham turf is sure to put a spring in your step and provide a brilliant day out with high-quality racing. Throughout the two-day meeting, there will be live music from The Quevegas Stage, the perfect place for refreshments and entertainment between races. - Cheltenham Jazz Festival – Montpellier Gardens – 30th April – 5th May
The Cheltenham Jazz Festival 2025 is one of the cultural highlights of the year. Big names already announced include the likes of David Gray, Corinne Bailey-Rae, Amadou & Mariam, Nubya Garcia and Jools Holland. - 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.
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.