Easy Peasy Weekends: A Fabulously Festive Weekend in Cheltenham

As well as the beautiful buildings to twinkle your toes, Cheltenham fills your stocking with plenty of things to do all year long: including pop-up markets, well-heeled cafés, bars and restaurants, world-famous festivals (the town is known as The Festival Town), and ornamental gardens, tree-lined avenues and green spaces.

Added to that, the surrounding Cotswolds’ countryside means you can swap the Regency elegance for a rural wintery walk on the nearby ‘wolds’ anytime you please.

Cheltenham is also small enough to dally around the main landmarks in a day but interesting enough to linger in for longer. Plus, the town is one of the most accessible for a UK weekend break thanks to Cheltenham Spa train station and excellent motorway and bus links.

Ad: This itinerary was tried and tested by our Editor-in-Chief, Claire, who joined Explore the Cotswolds and Danni Meets World for a hosted trip by Visit Cheltenham. If you buy or book something, we may earn an affiliate commission.

Easy Peasy Festive Cheltenham Weekend 

For festive retail therapy, Cheltenham hits the spot. At the heart of town, you’ll find your favourite retailers, with big names such as John Lewis and Primark holding court on the bustling main thoroughfares. Instead, turn heel and ‘shop small’ in the elegant Montpellier District of Cheltenham.

You’ll find Montpellier at the end of the Promenade south of the town centre. It’s here that the town’s famous spa waters were first discovered (curiously, by pigeons who were seen pecking at salts in the earth), although any trace of the original spa has long gone.

Originally developed in the 1830s, the Montpellier District is a fashionable area with a continental vibe thanks to distinct architecture; look out for the 32 caryatids that support the shop fronts. Today, it’s popular for its bars, cafés, restaurants and range of specialist shops.

We love Pink Vintage an award-winning, pretty in pink boutique selling home treasures, jewellery and art. For local unique gifts, try the Gloucestershire Guild of Craftsmen which sells fine craftsmanship (such as ceramics, mosaics and furniture) from designer-makers in the region. For bookworms, Rossiter Books is a wonderful independent alternative to the online giants with friendly staff, a book group, as well as signings and events.

Easy Peasy Festive Cheltenham Weekend 

Land in Cheltenham for a weekend in December and you can tick visiting a UK Christmas market off your list. During the festive season, Cheltenham’s pedestrianised Promenade and Long Garden (in front of the Municipal Buildings) become a sea of wooden chalets twinkling with fairy lights.

Expect a world of craft and gift creations from jovial local traders at Cheltenham’s Christmas Market. From artisan gins and cakes to original art and sculptures, you can easily pick up a yuletide treat for those on Santa’s nice list or for your (naughty) self – we won’t tell. There’s hot food and drink in abundance too, so you can melt away the icicles with a handmade crêpe or a warming mulled wine.

Bonus tip: If you’re keen to escape the chill, head into Cheltenham’s leisure hub, the Brewery Quarter. Here you’ll find well-known restaurants, plus indoor attractions to keep you toasty and entertained including Flight Club, Cineworld, Hollywood Bowl, Mr Mulligan’s indoor golf, and Escape Hunt.

Easy Peasy Festive Cheltenham Weekend 

Cheltenham is more than just skin deep. As you’ll discover on a guided walking tour with Blue Badge Guide Anne Barlett (who can tailor a tour to match interests). She’ll introduce you to the famous historical characters, residents, buildings and events that made the town what it is today, including King George III’s visit in 1788 and Cheltenham’s most renowned sons, composer Gustav Holst and polar explorer Edward Wilson – who were both born in Cheltenham.

The former composed ‘The Planets’ – a seven-part orchestral suite, written between 1914-1916. Whilst the latter was a doctor, naturalist, artist and polar explorer who perished on Scott’s expedition to the Artic in 1912.

On our festive weekend break in Cheltenham, we started our historical walking tour of Cheltenham in the The Wilson where we saw expedition artefacts, paintings and personal items belonging to Edward Wilson. He lends his name to this hugely impressive museum and gallery in the centre of the town, which has a wealth of exhibitions, collections and events all year long so is always worth a pit-stop.

To get up-close and personal with Gustav Holst, find time to visit his birthplace, the Holst Victorian House at number 4 Clarence Street. It is the only Victorian home open to the public and gives you a fascinating look at how the Holst family lived. You can even see the piano where Gustav Holst composed his famous suite.

Easy Peasy Festive Cheltenham Weekend 

You can’t miss The Queen’s Hotel in Cheltenham overlooking Imperial Square and Gardens. It stands like the top-tier of a grand wedding cake with 50 cream-white Corinthian columns and a neo-classical façade that shines out even on the darkest winter nights.

Modelled on the Temple of Jupiter in Rome by Robert Jearrad and his brother Charlies, this Grade II-listed building was first opened in 1838 and was one of the first purpose-built hotels in Europe. It was named in honour of Queen Victoria whose coronation fell the same year.

The hotel soon became a Mecca for nobility and royalty who flocked to the town to take in the spa waters and, in its time, it has welcomed through its doors eminent figures such as General Sir Charles Napier, Edward Elgar and Sir Arthur Conan Doyle.

On your Cheltenham weekend visit, head to The Queen’s for a festive brunch or glass of fizz in Victoria’s restaurant (which serves the best prosecco in the UK, ding dong) and has lovely views onto Imperial Garden.

Whilst you’re at The Queen’s, be sure to take a peak at the hotel’s impressive Christmas decorations and its original features: especially the handsome grand staircase. It is quite a marvel with historic wallpaper designed by Augustus Pugin, who masterminded the interior of the Palace of Westminster.

Bonus tip: Look out for festive pop-up bars around Cheltenham at Christmas. On our December visit, the Garden Bar in Imperial Gardens transformed into an Après Ski Bar with sheepskins, fairy lights, a ski lift photo spot and lashings of winter goodies including glühwein, hot toddies and tasty hot snacks.

Easy Peasy Festive Cheltenham Weekend 

At any time of year 15^th-century Sudeley Castle in Winchcombe (8 miles out of Cheltenham) is worth a detour. It’s the only privately-owned English castle to have a queen buried in its grounds: Henry VII’s last wife, Queen Katherine Parr who lived and died at the castle in 1548.

At Christmas, however, the castle transforms into a kaleidoscope of colour, light and sound as The Spectacle of Light takes over from the Tudor ghosts. Walk through the castle grounds after dark following the continuous illuminated trail – and prepared to be impressed.

There are glitter balls spinning in ancient oaks, water features and fountains dancing with fairy lights, 1,000 year-old buildings given new life with a show of spotlights, lanterns and beams, and enchanting ground installations that move with the cadence of the music as it fills the air.

Afterwards, warm up with mulled wine and hot doughnuts on the Castle Terrace. Trust me, whether you’re 6 of 46, Sudeley’s Spectacle of Light is a festive experience you shouldn’t miss.

Easy Peasy Festive Cheltenham Weekend 

For festive foodie highs, make tracks for The Nook on Five – Cheltenham’s first and only rooftop restaurant. Inside, the Nook is a rush of contemporary-retro glitz and glamour from the moment you enter, which you do on the ground floor. Here, there’s a trendy bar for a quick winter cocktail pre- or post-dinner or a splash of something without having to dine.

An elevator takes you to the fifth floor where gold-legged velvet chairs and marble-topped tables await, along with an attentive team to look after your coat, your thirst and your appetite. At one end of the restaurant, there’s a large free-standing cocktail bar manned by mixologists ready to stir up your weekend with something special. On weekends, the soundtrack is provided by a live pianist.

Aside from the food (which is excellent by the way), the biggest thrills come from the wrap-around floor-to-ceiling glass windows and balcony. During the day, views tumble in from as far away as The Malverns. And at night, Cheltenham sparkles in front of you. Wonderful.

Easy Peasy Festive Cheltenham Weekend 

Ellenborough Park takes first prize for enviable location. This sprawling 5-star hotel, restaurant and spa has sweeping views of Cheltenham’s famous racecourse thanks to its top spot at the Cotswolds’ highest point on Cleeve Hill, (just north of Cheltenham and reachable in 10 mins by car). A neat choice if you want to be out of town with miles of rural rambling routes on your doorstep and an excellent restaurant within your sights.

A cross between Hogwarts and Hampton Court Palace, dog-friendly Ellenborough Park has combined 500 years of history with a contemporary elegance. Inside the main hotel, you’ll find sparkling chandeliers, roaring inglenooks, stain-glass windows and oak-panelled rooms hung with oil paintings.

The main door into the hotel is pitted with bullet holes from the English Civil War and there’s the Tudor Rose of Henry VII in the Restaurant’s window. Seek out Johnathan the porter and he’ll regale you with stories of the history of the hotel.

Happily, the hotel has plenty of space with 61 rooms spread across various buildings – all of which nod to tradition whilst being comfortable and modern to boot. From Doubles and Classic Rooms with a cosy country house vibe to luxurious Deluxe Rooms and Suites with four-poster beds and claw-footed baths.

So, after eating like royalty in the exquisite fine dining restaurant, The Restaurant, you can roll into bed and sleep like a princess.

Neptune Apartments are the new kids on the block in Cheltenham but, boy, do they pack a style punch. Spread over four floors and housed within a gorgeous Georgian building, these self-catering apartments win best-looking in town, in my opinion, hands down.

There are 12 apartments in total (sleeping 2 adults); each named after different Cotswolds’ villages. They all have their own unique 5-star look and feel, and all comprise of a bedroom, kitchenette and/or breakfast bar, living space and en-suite.

Step inside and you’ll find original artwork on the walls, local toiletries in the deluxe bathrooms, top-of-the-range tech, and furnishings you’ll want to smuggle home. The only real difference in the apartments is their size – some have bigger kitchens and lounges, others are more studio-like. But even if you’re in one of the smaller units (like I was), you won’t feel hard done by.

Neptune Apartments come with a champion location, too. Find them just off the Promenade at the heart of Cheltenham, only a heartbeat away from the town’s shops, restaurants and bars. So you can roll from a bar to bed quicker than you can say ‘gingle bells’. Winner.