Our guide to Winchester Holiday Cottages & Apartments

Make holiday history with a cottage or apartment break in Winchester. Steeped in history, and with plenty to enjoy for the modern traveller, it offers one of the UK’s best city holidays with amazing architecture and attractions, fantastic food and drink, plus access to some of the country’s most stunning natural scenery.

Let’s start with the history. Inhabited since prehistoric times, and later visited by the Romans, Winchester isn’t short of a story or two about its rich heritage. Climb St Giles Hill for sweeping views of the city. Visit the breath-taking cathedral, where you will find 1,000 years of history presented in Europe’s longest medieval cathedral alongside beautiful wall paintings, carvings and contemporary art.  

More contemporary charms can be found in the city’s shopping districts, where high street brands rub shoulders with gorgeous boutiques and local crafts. Eat, drink and be merry in the many amazing pubs and restaurants, then venture further afield to stretch your legs on some stunning terrain. 

Things to do in Winchester

Whether enjoying a romantic retreat, family break or getaway with a group of friends, there’s plenty to enjoy in Winchester – some of it completely free. Take a trip to the Royal Armouries, City Museum, Discovery Centre and the brilliant city walk, and you will not only save money, but will greatly enrich your break! With more museums, zoos and railways, a break in Winchester offers perfect family fun.

Winchester also boasts a rich culture that’s perfect to explore on a cottage break. Jane Austen, John Keats, Sir Arthur Conan Doyle and more all celebrated Winchester in various works and in turn are celebrated today at a host of literary locations. Take a sunset walk through the city or follow in the footsteps of Keats with a romantic two mile stroll.

There are a host of seasonal events to enjoy in Winchester, making it a firm-favourite for a break at any time of year. Enjoy festivals of flowers, comedy, poetry, jazz, history and coffee all year round. It really is a destination with something for everyone.    

Winchester attractions

Alongside the city itself (more of that later!), a break in Winchester allows unrivalled access to a breathtaking part of the South Downs National Park. Alongside amazing walking trails there are National Trust properties and historic homes, lovely eateries and even vineyards to explore.

Visit the Winchester Science Centre and Planetarium for a more out-of-this-world experience on your break. This completely family-friendly attraction offers hands-on, interactive, science activities, a technology centre and the largest standalone planetarium cinema in the UK!

With such a rich history and heritage, you could spend all of your break in Winchester exploring its past. Visit the huge aisled expanse of the city’s Great Hall to experience the famed Round Table of King Arthur fame. With the working City Mill, Military Quarter, museums and cathedral, a wander around Winchester is like taking a trip through time!   

Our favourite Winchester restaurants

From culinary treats to family eats, Winchester is a glorious home of gastronomy. The River Cottage in Abbey Gardens is a great place to take the family for great food in a perfectly peaceful setting. More historic settings for fine food include the Cathedral Refectory – a lovely hidden gem – and the Chesil Refectory, fine dining in the city’s oldest house.

More familiar fare in Winchester includes Wagamama and Rick Stein, but there are plenty more surprises too. Visit world class Japanese and Thai restaurants and enjoy one of the finest meals you will ever have at The Black Rat, currently one of only two Michelin starred restaurants in Hampshire.  

Rick Stein Winchester

The first Rick Stein-owned restaurant to open outside of Cornwall. Offering fish and seafood with a nod towards our coastal heritage, this restaurant brings the freshest fish, simply cooked, and served in a sophisticated modern atmosphere.
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