Montpellier Gardens, with it's colourful bandstand, is one of many joys to discover on a weekend break in Cheltenham | City guide | Travel guide | Girl with a saddle bag travel blog

Cotswold charm in Cheltenham: A city break with a difference

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Ever thought about a weekend getaway to Cheltenham? Perhaps not.

But miss out on Cheltenham and you’re missing out on some of the most beautiful Regency architecture you can find anywhere in the UK, and some of the best artisan food and drink too. There’s much more to this pretty city than it’s horse-racing heritage – and I’m going to show you how to enjoy it with a twist.

If you’ve read my last post about our weekend in the Brecon Beacons, you’ll know that Ben and I decided to gift each other weekends away for Christmas.  My gift from him was a mountain getaway in Wales, whilst I surprised Ben with a weekend in Cheltenham.

You might be wondering why on earth I chose a Cotswold spa town as a counterbalance to the Brecons. It doesn’t sound like our usual jam.

But trust me on this one.

I’m not a stranger to Cheltenham, as I’ve visited it before.  But I was much younger and spent most of my trip in the basement bars of the city and well, I’d sort of missed out on the real reasons to spend a weekend here.  I briefly recalled some rather pretty architecture driving through though, and it stuck with me.  Needing to choose a location for our weekend getaway it suddenly flooded back to me.  Maybe we should give this town another shot?

With Bristol, Bath and Gloucester as near neighbours, the beautiful town of Cheltenham gets a little overshadowed.  But there’s much more here than meets the eye, and whilst it might be smaller than some of the surrounding cities it punches well above it’s weight.

Oh, and about that twist.  You might remember that we stayed in a shepherd’s hut on our last trip.  Well, I’d only gone and booked the same for our city getaway. (Feel free to make your own judgements about what this says about the two of us!).

Let me explain…

Our accommodation: Bergere shepherd’s hut

I didn’t start out looking for a shepherd’s hut.  It sort of found me.

I was trying to find a boutique hotel or a quirky B&B that might make an interesting change from our usual travel choices.  But failing to find one that floated my boat, or that was remotely within budget, I turned to my old faithful, Airbnb.  A five minute search turned up the usual array of spare rooms, sweet little B&Bs and granny annexes – and a shepherd’s hut.  I blinked, thinking I’d messed up my search somehow. A shepherd’s hut in the city centre?

But that’s exactly what Bergere is.

Tucked away in a corner of the charming area of Tivoli, just a stone’s throw from the city centre, Bergere is a contemporary shepherd’s hut with vintage style, but all the comforts of a boutique hotel room. Huge cosy cabin bed, perfect pocket-sized en-suite, beautiful little wooden kitchen with cupboards packed full of thoughtful touches. It was warm, outrageously comfortable and I immediately wanted to move in.

Our host, Kate, made us feel quite at home and very welcome from the moment we met her, but with our own entrance to the property and key in hand we didn’t feel like we were treading on anyone’s toes.

So whilst we took a moment to enjoy the cabin (whilst a spring shower poured down outside), we were soon off our to explore.

What to do in Cheltenham

Cheltenham is the perfect city for strolling.

Not too big, not too small, there are surprises around every corner and plenty to keep you busy for a couple of days.

I’d recommend that you start by scouting out some of the best architecture in town.

Exploring Cheltenham’s architecture

Cheltenham made it’s name as a spa town back in the Regency period – the early nineteenth century.  There’s no mistaking the buildings from this time, as the grand, symmetrical houses still stand out as some of the most beautiful in town.  And I’m going to make a bold claim.  I’d – perhaps controversially – rate it above the much-loved and somewhat more popular city of Bath (naysayers, tell me why I’m wrong in the comments!).

There are four key areas to meander around if you’re interested in Cheltenham’s history and want to find some of the finest architecture in the south-west of England.

Imperial Square

Quite literally in the centre of town, you won’t be able to miss Imperial Square.  Flanked on three sides by picture-perfect symmetrical townhouses, this little formal garden might not be much more than an expanse of green. But it’s an excellent foreground for the classic Regency architecture, and feels more like a smart part of North London than a provincial town way out west.  Look out for the Holst statue and fountain, Cheltenham was the composer’s birthplace and he’s celebrated in a few spots locally.

From Imperial Square, meander onto the Promenade.  This wide boulevard heads towards Cheltenham’s main shopping area and is lined with some of it’s most upmarket shops and more grand townhouses.


Just a few steps away from Imperial Square is the deliciously inviting area of Montpellier, home to Cheltenham’s most exclusive independent shops and restaurants.

Built from beautiful honey-coloured Cotswold stone, the shopfronts and little arcades are a stylish spot to stroll around, and delightfully colourful.  Montpellier Gardens sits next to the two main shopping streets and has a little more character to it than Imperial Square.  Check out the charming little gallery (next to the vibrant coloured bandstand) to see local art exhibitions for free.  We stumbled across a lovely little photography exhibit here on Saturday afternoon.

P.S. Look out for the Rotunda, the copper-roofed domed pavilion that’s now part of The Ivy restaurant.  Like us, this might not be in your league for dining out, but you can still appreciate the elegance of the 200 year old structure from the Gardens opposite.


Not far round the corner from Montpellier is Tivoli, a residential area packed full of delicious pastel-fronted terraced houses that look almost unreal.  Wander the streets here for a while and explore the delicatessen and independent shops along the main road.  It feels almost like the seaside here, with all the cheerful colours and Georgian architecture – only without the seagulls and chip-wrappers.  I rather fell for the place.

Cheltenham College

Whilst Cheltenham was making it’s name as a popular spa town during the early nineteenth century, it was also making it’s name in education.  Cheltenham College was founded in 1841 as an exclusive public school, and it’s left it’s mark on the city’s architecture.

A skip and a jump away from the city centre is the college chapel and library, and whilst these aren’t landmarks I’d normally go out of my way to see, in Cheltenham they’re pretty special.  Constructed from soft Cotswold stone, they’re beautifully graceful and more than reminded me of the Colleges of Cambridge University (I think it’s fair to say they borrowed more than a little from their designs).

As with Tivoli, it’s well worth a wander here as there’s plenty to surprise you.

Park Life

Aside from Imperial Square Gardens and Montpellier Gardens, there’s much more than meets the eye when it comes to green spaces in this city.

Pittville Park

Head north from the main shopping areas of Cheltenham and you’ll start to see signs for Pittville Park sprouting up.  These will take you to the city’s largest green space (worth a stroll in it’s own right) and the magnificent Pittville Pump Room.

The pump room is a huge part of what put Cheltenham on the map as a spa town, as the largest of all spa facilities built in the town.  Sat in the lush surrounds of the park, this grand building exudes Regency charm and looks straight out of a Jane Austen novel.  It’s the jewel in the crown of an already quite lovely park in a rather smart neighbourhood – and well worth the walk to get to.

Other green spaces

Sandford Park is the largest green space near the city centre and a nice little spot down by the river.  With a big play area, it’s a good place to swing by if you’ve got little ones with you.

If you fancy strolling further afield, trying heading towards the campus of the University of Gloucester, south of Tivoli.  I meandered through this part of town on my morning run and it’s a delightfully verdant area that’s easy to otherwise miss.  It’s also surrounded by some of the city’s grandest Victorian villas – it’s worth a look if you’re keen to discover more of Cheltenham’s outstanding architecture.

Eating and drinking in Cheltenham

Coffee and cake

With all the wandering and exploring there is to do in Cheltenham, I think it’s an excellent excuse to be well-fuelled with coffee and cakes.  So, with any excuse seeming a good one, we set out to try as much as possible.

The Swallow Bakery

We headed straight to the Swallow Bakery when we arrived on Saturday morning.  Whilst the decadent displays of homemade cakes lured me in, it’s actually a great place to stop for coffee close to the Imperial Square and the main shopping streets of Cheltenham.  Ignore the fact that it’s located in the ugliest building in town (the 1970’s called, and they want their concrete structures back), it’s cosy and convivial inside.

The Swallow Bakery | The Quadrangle, Imperial Square, Cheltenham

The Scandinavian Coffee Pod

Not being able to resist another coffee stop, we also gave The Scandinavian Coffee Pod a try.  Completely different in every way to The Swallow, you won’t be able to miss it’s angular, modern fascade if you stumble across it.  And here, it’s all about the coffee.  Serious coffee -this is is a place for enthusiasts.  Ben was in his element being served our (admittedly delicious) coffee in a glass pot on a wooden board, with a delicate china bowl to drink it from.  A goats cheese bagel convinced me this coffee shop wasn’t a step too far, and was actually a rather enjoyable stop for a drink and a bite to eat.

The Scandinavian Coffee Pod | The Studios, Royal Well Place, Cheltenham

Baker & Graze

If you want a real bakery (not just somewhere to sup coffee) head immediately to Baker & Graze on the Suffolk Road.  This artisan bakery not only makes it’s own bread and pastries, but it’s also a great place to stop and while away a Sunday morning.  Their extensive brunch menu gives you plenty to choose from – I went for avocado toast and bacon whilst Ben went for Shahshuka eggs.  It’s definitely more lunch than brunch, especially when you factor in coffee and cinnamon bun like we did, but it is darned good.  I’d very happily go back.  Immediately.

Baker & Graze | 48 Suffolk Road, Cheltenham

Dinner in Cheltenham

The Tavern

I stumbled across the Tavern online, looking for somewhere independent but informal to eat.  Think pub classics with a twist, posh burgers and side dishes big enough to eat as a main in their own right.   It fitted the bill perfectly, and as a bonus they had the same French Dip sandwich I’d fallen for on their website on the night we went to eat.

It was pretty packed on a Saturday night, so I’d strongly recommend booking well ahead if this sounds like your cup of tea.  And whatever you do, order the sticky toffee pudding ice cream sandwich for dessert.  It’s every bit as good as it sounds.

The Tavern | 5 Royal Well Place, Cheltenham

Drinks in Cheltenham

Jessop House

What would I recommend doing if spring showers interrupt your afternoon of exploration?  Well, there’s worse things to do than head to Jessop House and indulge in a beer or three.  Owned by (relatively) local brewery the Wild Beer Co, it has an ever-changing menu of weird and wonderful craft beers (and delicious bar snacks).  Importantly, this meant Ben was very happy on his belated Christmas trip.  Equally importantly, it makes it a fun and interesting stop for pre-dinner drinks.

Wild Beer at Jessop House | 30 Cambray Plac, Cheltenham

Sandford Park Alehouse

At the risk of living up entirely to our own stereotypes, we also popped into the highly recommended Sandford Park Alehouse.  We evidently can’t help ourselves.  A serious enthusiasts pub, it’s won bucket-loads of awards for it’s diverse and well-kept beers.  As with Jessop House, it’s got a cosy atmosphere and great city centre location – just a slightly older crowd.

Sandford Park Alehouse | 20 High Street, Cheltenham

Cheltenham might have been a left-field choice for a weekend getaway, but it more than lived up to my expectations.  If you’re based in the south-west it’s a great day out, but if you can stay a little longer you’ll be rewarded with more captivating discoveries as you tread further afield.

As for the shepherd’s hut, I’m sold.  It had more charm than any hotel room could have offered us.  And we had the added bonus of being able to enjoy what felt like a rural idyll whenever we wanted.

So here’s to Britain’s less well-known cities – I’m ready to explore some more of them.

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  • Bernie
    Posted at 15:24h, 14 April Reply

    I don’t live that far from here, but I could certainly be persuaded that an overnight stay would be worthwhile. It’s a lovely town – a bit like Leamington which also has that Georgian spa vibe going on. That shepherd’s hut is just gorgeous! There looks like some seriously good eating to be had too; it should persuade me to expand my horizons beyond Whole Foods in Gloucester next time we’re heading that way.

    • Alice
      Posted at 19:59h, 14 April Reply

      I’ve never been to Leamington, but if it’s half as good as Cheltenham I need to make a beeline there! I’d thoroughly recommend an urban shepherd’s hut just for the experience, no matter how far from home. I’ve done a couple of similar stays but nothing quite like this one. Thanks for your kind words 🙂

  • Zara
    Posted at 18:19h, 31 March Reply

    It’s a running joke amongst my friends that I travel all around the world but never take the time to see my own beautiful country! This is something I’m working on ha! I’ve lived in the UK my whole life and never been to Cheltenham!

  • The Curious Sparrow
    Posted at 13:39h, 31 March Reply

    I’ve never visited Cheltenham before but it looks charming. I love colourful houses so Tivoli is definitely somewhere I’d visit

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