I Fell in Love with The Cotswolds as an American Woman in My 40s
I think it’s safe to say that if you’re an American woman who was in their 20s in 2005, then you’ve dreamed of being Cameron Diaz in the movie The Holiday (just me?!). I could have never imagined just how much I would fall in love with The Cotswolds as an American on my very first time visiting.
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The First Time I Fell in Love with the Cotswolds
In 2022, I booked my very first trip to Europe during the holidays. For background – I was an elementary school teacher from 2007 – 2020, so I had only ever taken trips to Europe during the summer. I had NO idea how much I would enjoy Europe in the other seasons of the year, but after leaving my teaching career and going full time with my education business of creating resources and selling them online, I finally had the flexibility to travel any time of the year.
Now, technically, Cameron Diaz wasn’t in The Cotswolds in the movie The Holiday. However, we all found out that the fictitious cottage she stayed in was very similar to the style of homes you’d find in this newly discovered (by outsiders) area in the English countryside.
The Private Tour of the Cotswolds That Changed Everything
When the day arrived for me to take the train to Oxford to meet my driver, a snowfall almost completely derailed everything. They don’t get snow in the area often, so when they do, nobody’s typically driving around in it. Luckily for me, my driver didn’t bail, and I was able to take an Uber to meet him after my train was canceled. Little did I know, this one trip would COMPLETELY change the trajectory of my life. (We’ll get to that another time, but if you follow me on Instagram, you probably know where this is going).
When I finally got to Oxford, I met my guide/driver/photographer, Cuma, and learned that I was in for a completely epic day of seeing some of the most beautiful villages with fresh snow on the ground.
Here’s where we went (in order): Burford, Bourton-on-the-Water, Lower Slaughter, Stow-on-the-Wold, Broadway Tower, Snowshill, and Broadway. In each place, Cuma captured photos of me, which slowly got better as I got more comfortable.
Stop #1
Burford
Often called the gateway to the Cotswolds, with a High Street that slopes straight down to the River Windrush. This is where I couldn’t stop myself from photographing every door, and it’s an easy first stop for coffee before heading deeper into the region.
Stop #2
Bourton-on-the-Water
Nicknamed the Venice of the Cotswolds because the River Windrush runs right through the village, crossed by a handful of low stone footbridges. It’s also home to a model village, a miniature replica of Bourton itself built at a 1:9 scale. I visited it while I was there and highly recommend it!
Stop #3
Lower Slaughter
One of the quietest and most photographed villages in the Cotswolds, built along the River Eye around an old mill with its water wheel and tall brick chimney still standing. There’s no High Street full of shops here, just honey-colored cottages and a slower pace.
Stop #4
Stow-on-the-Wold
A historic market town built around a wide market square, once one of the busiest sheep-trading hubs in England. Don’t skip St Edward’s Church, where the north door is framed by two ancient yew trees, said to be one of the inspirations for Tolkien’s Doors of Durin.
Stop #5
Broadway Tower
An 18th-century folly completed in 1798 for the 6th Earl of Coventry, designed by architect James Wyatt from an idea sketched out by landscape designer Capability Brown. It sits near the second-highest point in the Cotswolds, and the walk up is worth it for the views across several counties.
Stop #6
Snowshill
One of the smallest and least commercialized villages in the Cotswolds, and my personal favorite for that reason. It’s home to Snowshill Manor, a 16th-century house once owned by the eccentric collector Charles Paget Wade, who filled it with more than 22,000 objects before giving it to the National Trust in 1951. This is my absolutely favorite village!
Stop #7
Broadway
Often called the Jewel of the Cotswolds, with a wide grassy High Street lined with chestnut trees and golden stone buildings. It has a slightly more polished feel than the smaller villages, with plenty of tea rooms and shops to wander through.
Though the day was mostly spent driving from village to village, a little time walking through each and taking photographs, and essentially just getting an overview of each spot… I was captivated. I knew that I had to go back and really dive into this part of the world.
When we first arrived on the High Street in Burford, I was mesmerized. We got out of the car to walk and grab a coffee and I had to stop myself from taking a photo of every single door. Each one was more picturesque than the next. The village captured me in a way that I couldn’t put into words. I knew that I needed to find a way to return and spend more than just a few hours here.
Two Years Later: Three Trips in Three Months
It was two years before I prioritized another visit to The Cotswolds and little did I know that I would ultimately plan three trips there in just three months.
First, I planned a fall trip to Europe where I spent a 6 week trip in Denmark, Sweden, Germany, the Netherlands, and finally, England. This time it was October 2024 and I spent a few days in the Cotswolds, opting for an Airbnb in a small village just outside, in a village called Alderton in Gloucestershire. I ended up extending my stay in the area and booking a second place in Chipping Norton for a couple extra nights.
During that short visit, I experienced my first Sunday roast ever at the village pub, being welcomed with open arms by the owners. They not only shared a book about their village with me while I dined, but I was also invited to come back later in the week to watch their darts league (I LOVE darts!)
I rented a car on this trip, which allowed me the flexibility to explore more villages on my own. I went to Burford, Chipping Norton, Snowshill, Broadway, Stratford-Upon-Avon, Bourton-on-the-Water, and even a scone making experience in thatched cottage in Hanwell.
Even though I was there for four nights solo, I felt safe, comfortable, and as though I was meant to spend more and more time there. This wasn’t going to be the end of my love affair with the Cotswolds.
A Birthday Getaway and Cotswolds Christmas
It wasn’t long before my next trip to the Cotswolds, spending an extended weekend for my birthday two months later in December 2024. For that trip, I stayed just on the edge of the Cotswolds near Evesham in a tiny little one bedroom cottage. This trip was all about experiencing the area at Christmas time and to have a cozy getaway for my birthday.
I finally got to meet Ali Woods (Ali in the Cotswolds), one of my favorite creators that I’ve connected with through social media, and see the English countryside decked out for the holidays.
From the villages being covered with lights and decor to an evening light show at Sudeley Castle and cozy meals in some of the most adorable pubs with roaring fireplaces… it’s safe to say that I fell in love with this place even more than I already was. This ultimately led to me deciding to do a…
it’s safe to say that I fell in love with this place even more than I already was
Five Weeks, One Workcation, and a Life I Didn’t Expect
5 week solo winter workcation in the Cotswolds just a few weeks later! Yes, I planned a massive trip on a whim and booked some very last minute cottages in some of the cutest villages in the Cotswolds where I planned to simply cottage hop from the first week of January to mid-February.
I chose the least attractive time to spend over a month in one of the most picturesque places in the world, but I didn’t care. This was about taking a time of the year when I’m typically hibernating, depressed, and just spending time indoors doing work from home. I’m a travel content creator and writer, so for me it was the perfect place to work remotely. So why wouldn’t I just do the same exact thing I would have done in Atlanta, but this time in another country?
This trip was nothing less than TRANSFORMATIVE.
This trip was nothing less than TRANSFORMATIVE. It wasn’t perfect, and I wasn’t constantly doing things or entertaining myself. The whole goal was to feel like I lived in the Cotswolds. To connect with the villages, with the people there, and be productive with my business. I wanted to experience what it was like to immerse myself in the English countryside and it was such a great decision.
Not only did I reconnect with myself, but I created relationships with locals and even joined a women’s group for social and networking opportunities. I went on my first countryside walk with a group of local women all looking to create connections and I was surprised at how welcoming they were while knowing I don’t even live in the country. They made me feel less like a visitor and more like I really belonged.
The entire 5 weeks was magical. I spent a week at the most picturesque cottage in Chalford (southern Cotwolds), a week in an adorable cottage in Winchcombe, a few nights in places like Stratford-Upon-Avon, Llanerch, South Wales, and Thurgarton, and ending my trip at a cottage in what is now my favorite Cotswold town – Chipping Campden. I really just spent time enjoying life in a completely different way. The English countryside has a different pace and I did my best to adapt to it.
How a Cotswolds Trip Led to a Transatlantic Relationship
Toward the end of the 5 week (just for kicks), I went on Bumble and had a little fun swiping on different men and seeing what kinds of single men were living in the area. To my complete surprise, I ended up matching with a guy that I continued to talk with after leaving. I tried to meet up with him while I was still in England, but he was traveling and our schedules just didn’t work out.
Somehow, we continued messaging, and then messaging turned into video calls. Video calls turned into me booking a flight back to the UK in the month of April to meet him in person and see if we could hit it off in real life as much as we did over the phone. Now that man is my boyfriend of over a year and a half, as of writing this blog post in August of 2026. I now am traveling back and forth to the UK.
While my partner, Steve, does not live in the Cotswolds, I still have connections there and drive there frequently to participate in some networking events and social events with the group that I’ve joined called the Cotswolds. Steve lives in Leicestershire, and we are navigating a relationship that is transatlantic. When I’m here for longer periods of time, I am adapting to life in England when it’s not a vacation.
Why I Keep Going Back and Why You Should Visit the Cotswolds as an American
What started out as romanticizing my life and trying to find ways to experience joy in different ways through travel, I have ultimately found an incredible partner and fallen in love with a part of the world that I never would have imagined. I am continuing to fall in love with pieces of this country every time I visit. I think it’s hard not to fall in love with the Cotswolds, which is why I continue to go back. I think it’s a place where most people would find it hard not to love, whether you’re a woman in her 40s wanting to live out that Cameron Diaz holiday experience, or you’re a couple or a family looking for quaint areas to visit.
I highly recommend taking time to travel to the Cotswolds. It is one of the most beautiful places in the world. It has wonderful people that will welcome you with open arms, and I have a feeling you won’t visit just once.
Where to Stay in the Cotswolds
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Things to Do in the Cotswolds
Looking for fun activities to do in the Cotswolds? Use this list to help with planning.
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