The Cotswolds, England: Insider’s Guide

The insider advice on this page is from one of Wendy’s Trusted Travel Experts for England, Ireland, and Scotland: Jonathan Epstein of Celebrated Experiences.

Trusted Travel Expert

Jonathan Epstein

Jonathan’s deep knowledge and relationships allow him to design trips that include picture-perfect Cotswold cottages, the latest Michelin-starred Scottish restaurants, and the most extraordinary Irish castles—and he and trusted deputy Katie Stewart always include the most scenic drives between all those fairytale properties and otherwise-hard-to-book restaurants. You’ll also benefit from the duo’s close relationships with colorful hoteliers and star chefs, not to mention their friends all over the U.K. and Ireland, from whiskey distillers to crystal cutters to cashmere-sweater weavers. Of course, they can also snag tickets to special events (including Wimbledon and Premier League Soccer).

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Expect trips orchestrated by Jonathan to start at $1,800 per day for two travelers, plus a $700 planning fee.

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Things to Do and See

Most overrated place
If cars are what you fancy, you can do much better in Britain than the Cotswold Motoring Museum’s small collection in Bourton-on-the-Water. The town itself, while lovely in slower times of the year, can be quite crowded in summer as well.

Most underrated places
When people think of the Cotswolds, they think of villages, walks, pubs, and gardens—but generally not castles. Sudeley Castle, however, in Winchcombe, probably has more connections to royalty—especially the Tudors—than any other stately home outside greater London: It’s where Henry VIII’s last wife lived, and where King Charles I took refuge during the Civil War. The gardens are magnificent as well.

Sudeley Castle has a long and complex royal history. Photo: Shutterstock

While there are many charming villages in the valleys and hilltops of the Cotswolds, Stanton enjoys a particularly picturesque location, terraced along a hillside and a bit off the main road. Some of the most beautiful views over the countryside come from the Mount Inn, a pub perched at the top of town.

Hidden gems
Berkeley Castle has been inhabited for the past 850 years by the same family that built it. For centuries the Berkeleys have been tied to the success of the monarchy. They fought well…and married well. King Edward II, before his untimely death, was imprisoned here by Queen Isabelle and Roger Mortimer. Learn all the house’s (and, perhaps, some of the family’s) secrets on a private tour.

Though the gardens of Rousham House are open daily and are a must for garden lovers, the house’s interior is generally closed to the public.  Jonathan, however, can arrange for his guests to tour both.

Bragging rights
Jonathan can arrange for a guided visit to a private Elizabethan-era family home, built of yellow Cotswold stone and known to Poldark fans. Only two families have ever owned this stunning property, and it’s a member of the latter family who leads the private tour of its cavernous rooms and 17th-century tapestries.

The Cotswolds’ famous yellow limestone on display in Upper Slaughter. Photo: Jonathan Epstein/Celebrated Experiences

How to spend a lazy Sunday
Walking the countryside! The Cotswolds are lined with beautiful public footpaths. These trails, which literally cross people’s property, have been here for hundreds of years, well before modern roads. You can leave your country hotel or village inn and go on dozens of walks across fields surrounded by sheep, cows, and other rural wildlife. Walks could be as short as half a mile (Upper Slaughter to Lower Slaughter) or longer (the four miles from Broadway to Chipping Campden, say), and you can combine several to fill as many hours as you please—or hop from village to village, always on the lookout for a quaint pub.

Best for thrill seekers
Without a question, Cheese Rolling! If you have no idea what this is, go to Youtube now and enjoy.

Where to Stay and What to Eat

Hotels worth the splurge
Foxhill Manor combines the intimacy of a small, boutique hotel with the amenities of a larger property: Its eight individually designed rooms—built in a historic Arts-and-Crafts country home that has been carefully updated for the 21st century—are located on the grounds of the Dormy House Hotel; guests have access to that property’s restaurants, pool, and spa. Jonathan’s travelers enjoy free breakfast, Wi-Fi, and guaranteed upgrades at the time of booking.

Estelle Manor is a 5-star resort that opened in 2023 as a sister property to world-renowned Gleneagles. It offers state-of-the-art wellness facilities, a range of dining options, falconry, and even axe-throwing in an idyllic countryside setting 30 minutes from Oxford and just over an hour from Heathrow. For families craving a more immersive countryside experience, Estelle Manor also has private cottages.

Best-value hotel
Nestled in the heart of one of England’s most quintessential Cotswold villages, The Painswick blends into the town’s yellow Cotswold stone landscape and features contemporary country-house style. Tramp along the Cotswold Way, cycle through the rolling hills, or relax in their lovely spa. Jonathan’s travelers get upgrades based on availability, chocolates made in the Painswick kitchen, noon checkout, and free breakfast. The hotel also features a three-bedroom cottage, perfect for families.

The Painswick has 18th-century bones and all the modern comforts of a boutique hotel. Photo: The Painswick

Restaurants the locals love
This region is one of Europe’s finest craft food destinations for a number of reasons, among them the incredible abundance of locally sourced organic offerings, and the skilled London chefs who have fled here to hone their craft in a more relaxed atmosphere. Here are a few such options where tourists are not the rule but the exception:

Wild Rabbit uses mostly local ingredients in its fine-dining takes on British cuisine.

Located in Kingham, Wild Rabbit is the sister restaurant of Daylesford, the well-known organic farm shop located a short distance away. This is a great spot to rub elbows with Cotswold elites and posh Londoners who have escaped to the countryside for a break. There’s a nice selection of artisan beers and traditional ales to pair with your meal.

Bell at Sapperton is great for Sunday lunch. They serve a top-quality roast, and the place is always brimming with locals.

The Village Pub is an authentic pub in Barnsley now under new ownership and connected to the innovative Pig hotels. It has a lovely ambiance and delicious food.

Dishes to try
While there is no single iconic Cotswold dish, the area is home to many exceptional foods. For example, asparagus from the Vale of Evesham is a must in summer, as are Pershore plums. Sample many beautiful local cheeses—St. Eadburgha, Single and Double Gloucester, Cerney Goat Cheese—at the Cotswold Cheese Company in Moreton-in-Marsh. Do also indulge in some of the excellent local game, such as venison, pheasant, partridge, and rabbit.

Meal worth the splurge
The dining room at Whatley Manor, one of England’s finest hotels, offers Michelin-starred dining in an elegant, yet relaxed setting. Opt for the tasting menu; the kitchen sources from local producers vetted for their sustainable credentials.

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