Search Cowes cottages

Holidays in Cowes

An ancient Viking settlement, home to the oldest and largest regatta in the world

Cowes harbour

A vibrant and sporty town on the north coast of the Isle of Wight, Cowes especially comes alive during its world-famous regatta. Do not be fooled into thinking that this seaside town is just about sailing though, it also hosts a myriad of other sporting and cultural events throughout the year.

Without doubt, the most exciting time to go is Cowes Week – with up to 40 races per day and with over 1000 boats, you will always find something to watch. The town is buzzing with people and celebrities, so if people watching is your thing, this is the time to go! If only one of your party is a keen sailor, head to one of the many cocktail parties or musical events set up in huge marquees on the Esplanade. The event culminates with a beautiful firework display over the water, best watched from a yacht if you can.

There are lots of pretty shops and pavement cafes in the town - why not stop at one of the many restaurants too? There are various places to charter boats in Cowes and for a picnic on the water, head to the Food Hamper delicatessen in Cowes High Street who will make up a wonderful basket of goodies for you. Be sure to take an evening sunset stroll along the promenade and stop for an ice-cream at one of the many parlours – the view is spectacular.

Cowes offers a fascinating history – during the 11th century, the Vikings created settlements on both sides of the river Medina, using it as a route for raids. Due to various attempts at French invasion over the years, two castles were built on either side of the river under the order of Henry VIII in 1539. The east-side castle was soon abandoned after a peace treaty with France but the west-side castle was occupied by the military until 1854 when it was bought by the Royal Yacht Squadron. It went on to be the world’s first yachting centre, maintaining links with the British Royal Family as well as boasting cosmopolitan members such as Prince Rainier of Monaco, the Aga Khan and King Constantine of Greece.

"A vibrant and sporty town on the north coast of the Isle of Wight..."

If your sea-legs are having a rest, spend an afternoon browsing the maritime museums and art galleries in the town. A hidden gem is the Classic Boat Museum, great fun for boat enthusiasts. Just remember that the town is on two banks so if you want to visit both sides, you need to hop aboard the Chain Ferry!

Later head to Northwood Park, not far from the centre of Cowes. The perfect place for summer evening strolls, this gorgeous house welcomes children and pooches and offers cream teas on the lawn during the summer. The house once hosted high society soirees during the Victorian era and offers exhibitions and events as well as an outdoor family theatre.

We have some lovely holiday homes on the Isle of Wight. Why not view our collection of Isle of Wight cottages for inspiration?

While you’re there

Cowes Week

The town's most popular event, and one of the world's largest regattas, with more than 1000 boats

Classic Boat Museum

Discover hundreds of years of maritime history at this hidden gem of an attraction

Northwood Park

A gorgeous country house perfect for parkland strolls

Join thousands of people already enjoying successful letting with

Do you have a property that you're interested in letting? To find out more about letting with us, simply get in touch with our friendly team today.