Winter in Essex offers a unique charm, with historic towns, cosy retreats, and plenty of seasonal activities to enjoy. Whether you’re planning a festive break or a quiet countryside escape, these destinations are perfect for a short winter getaway. Here are some of the best places to explore – and why you should book on Airbnb for a comfortable base.
Book on Airbnb in Harwich: A Coastal Winter Escape
Harwich is steeped in maritime history and comes alive in winter with its charming harbour views and crisp seaside air. Take a bracing walk along the waterfront, visit the Redoubt Fort, or enjoy fish and chips in a traditional pub by the sea. A short-term holiday let in Harwich gives you the freedom to explore both the coast and nearby countryside. With DRV connections linking the town to the wider Essex coast, Harwich is an excellent choice for travellers who want history and fresh sea air combined.
Book on Airbnb in Romford: Shopping and Winter Fun
Romford is known for its vibrant shopping scene, making it an ideal winter destination for those who love a bit of retail therapy. The Liberty Shopping Centre offers everything from high street names to boutique finds, while the Romford Market provides seasonal produce and gifts. For family fun, the Sapphire Ice & Leisure Centre offers ice skating all winter long. Staying in a local short-term holiday let gives you a homely feel while being close to London, with DRV routes making travel easy.
Book on Airbnb in Chelmsford: Festive Spirit in the City
Chelmsford, the only city in Essex, shines during the festive season. Bond Street is lined with Christmas lights and seasonal markets, while Hylands Estate hosts winter events and trails. You can enjoy riverside walks, cosy restaurants, and even day trips into London from here. By choosing a short-term holiday let in Chelmsford, you get flexibility and space – perfect for families or groups travelling together. DRV access ensures smooth journeys into surrounding towns and countryside.
Book on Airbnb in Brentwood: Countryside Walks and Cosy Pubs
Brentwood is a winter favourite thanks to its mix of woodland trails and cosy countryside pubs. Weald Country Park is a great spot for frosty walks, and nearby pubs with roaring fires provide the perfect post-walk treat. Brentwood also hosts festive events and markets during the winter months. Booking a local short-term holiday let ensures you’re right in the heart of Essex’s countryside charm. DRV travel options make Brentwood well connected for exploring further afield.
Book on Airbnb in Colchester: History and Winter Markets
Colchester, Britain’s oldest recorded town, is a magical place in winter. Colchester Castle Park transforms with lights and markets, and the historic streets are perfect for festive shopping. Families can enjoy Colchester Zoo, which stays open year-round, or take winter walks through Dedham Vale. With a wide choice of short-term holiday lets, Colchester is a versatile base for history lovers, families, and couples alike. DRV transport links make it easy to travel across Essex or further into Suffolk.
Final Thoughts
Essex has something for everyone during the winter months, from coastal charm in Harwich to vibrant shopping in Romford, city lights in Chelmsford, countryside walks in Brentwood, and historic adventures in Colchester. Choosing to book on Airbnb gives you flexibility, comfort, and value – ideal for a memorable winter escape.