Winter Breaks in Chester

Chester is a truly unique city, brimming with history, culture, dining, and all kinds of adventures to be had. Experience Chester's finest with a luxury break, treat yourself to afternoon tea, stay in a 5* hotel, dine in a stunning restaurant, visit award winning attractions and travel in style by booking first class with Transport for Wales. 

Sitting on its 2000-year-old foundations, and with plenty of evidence of its fascinating past, Chester is just as vibrant and alive as ever, making it a perfect place for you to escape this winter. Winner of the iTravel Staycation City of the Year, Chester can be what you make of it: From a perfect city escape filled with world-class attractions and events, or a foodie paradise boasting everything from Michelin-starred cuisine to some of the best street food, to an exploration of thousands of years of history and culture, and a place to explore new adventures like kayaking, stand up paddleboarding and reconnecting with nature.

The city is always alive with unforgettable things to do. Home to one of the UK’s most popular attractions, Chester Zoo, you can experience the whole world in a day. Take in the magnificent views of the city from prime position onboard ChesterBoat on a sightseeing cruise. And with a fully-stocked bar, why not enjoy a drink as you take in Chester in all its glory. And you won’t want to miss some of the events that really make the city come to life, with everything from live music to world-class theatre, and craft beer to cocktail celebrations, book your trip to Chester and secure your place at some unmissable events.

You’ll surely be intrigued by Chester’s historic and cultural landscape, from its Roman walls and Medieval facades to the magnificent Cathedral and ancient church grounds. You can see just about every part of the nation’s history in Chester, and whether you want to explore this history and culture yourself or with a guide, the city’s past truly comes to life. You can explore the city with Roman and Medieval soldiers, delve deep into the history of the walls and the city at large, and experience the city’s past with innovative, interactive displays in our world-class museums. Chester is perfect for escaping the everyday by escaping to the past.

If you’re tired of cooking at home, let Chester’s many exceptional restaurants, bars and food experiences help you to escape the everyday. Why not craft your own signature cocktails, sample artisanal spirits, or experience life as a micro brewer, creating your own beer! Awaken your palate with some of the finest wines from around the world and come away a wine expert (or just having tried some very fine wine!). And let’s not forget about the food. Chester, already renowned for its range of superb restaurants, from Michelin-starred tasting experiences and microseasonal menus, to exceptional vegan, vegetarian and plant-based options and truly innovative street food, Chester really is for foodies. Why not tour the city with a foodie expert on a city food tour to try some off-menu treats or sit back and relax in some of the most intriguing surroundings to enjoy that quintessential British treat – afternoon tea (perhaps with some champagne to boot!).

And Chester is full of active adventures, whether within the ancient city walls or into the gorgeous Cheshire countryside just on the doorstep - winter is the ideal time to get outdoors and embrace the season. Delve into the city’s past with a twist on a cycling or running tour to get in a unique workout as you learn. Or take to the beautiful River Dee on a kayak, canoe, or paddleboard whether you’re a complete novice or pro, there’s an adventure for everyone. And Chester is the perfect base for a rural escape. Connected easily to destinations throughout Chester and beyond, your escape to Chester can take you into the Welsh hills for some unrivalled views, or perhaps into some of Cheshire’s finest scenery where you can enjoy treetop adventures, forest Segways and all kinds of outdoor pursuits.

Chester is an unmissable escape and a short break to this historic, vibrant city should not be missed. Check out our inspirational guides to give you some ideas for your break to this fascinating city this winter.