Cowes is the Isle of Wight’s main port and just a quick ferry ride across the Solent to Southampton. It’s also a pretty town, with sandy beaches and a maze of narrow streets, packed with independent businesses. Nestled on the banks of the River Medina, on the island’s north coast, this welcoming community has a rich maritime history and remains a centre for sailing. Whether you are planning on exploring the sweeping estuary, rambling over soaring white clifftops or relaxing on one of the area’s many dune-backed beaches, Cowes holiday cottages are perfect for a relaxing break on the Isle of Wight.

Cowes lies on the river’s western bank, facing East Cowes on the opposite side of the water, and the two towns are connected by a floating bridge, or chain ferry. Since the 1800s, Cowes has been the home of international yacht racing, with the oldest regular regatta, Cowes Week, in the first week of August. Wander into the town centre from your holiday cottage in Cowes and you will discover some of the island’s most beautiful historic architecture, including the grand 18th century houses of Northwood and Westbourne, and a beautiful esplanade with views across the Solent, to the mainland.

10 cottages found 10 match all criteria.

Unwind at Solent Lawns in Cowes, Isle of Wight, and find the perfect getaway for sailing fans and weekenders alike. Take in the picturesque sea views of the Solent and holiday in style at Solent Lawns, a highly desirable 3-bedroom seaside holiday cottage ideally situated above the Gurnard seafront.

Pinkmead is a waterfront cottage in Cowes, on the Isle of Wight, which boasts its own private jetty and boat shed as well as beautiful water views, 24 acres of gardens, a sauna, an open fire and pizza oven. The pet-friendly cottage also boasts a separate studio, plus rare seclusion and tranquillity.

For a couple of families or a gathering of friends, Lifebuoys is a large and luxurious coastal cottage in Cowes with five-bedrooms, and three-baths, a magical portal to all the wonderful holiday attractions on the Isle of Wight. Sleeps 14.

Bright, modern, and offering plenty of space for the whole family, Dandelion is a large coastal cottage situated perfectly in Cowes Village on the Isle of Wight, offering a relaxing escape that’s still ‘close to it all’. Pets welcome.

  • Sleeps 9
  • Bedrooms 4
  • Bathrooms 1

Nutcroft is a graceful period Isle of White holiday home in Cowes within a short walk of the town’s marinas, bars, bistros and restaurants. The family friendly house sleeps 4 in two stylishly decorated bedrooms and is thoughtfully equipped from Bluetooth music systems to the Tassimo coffee machine.

Take a scenic ferry ride to the breathtaking Isle of Wight, where Pilot House will be your well-maintained and large home for your holiday from which you will explore the many sights and activities the Isle of Wight has to offer, including the spectacle of Cowes Week.

Woodyear House is a unique restoration of a haberdashery in the sailing resort of Cowes on the Isle of Wight blending ornate tradition with contemporary style. The large waterfront property is a family-friendly 4-bedroom coastal cottage with beautiful coastal views. Pets welcome.

Fitzroy, an Isle of Wight holiday cottage in the sailing resort of Cowes, is a very popular location, that attracts regular returning guests. Fitzroy, is very spacious and comfortable, enough to house a whole family easily. Pets welcome.

  • Sleeps 6
  • Bedrooms 3
  • Bathrooms 2

Spinnaker House is a modern, spacious and contemporary holiday home in Cowes on the Isle of Wight. The child-friendly house sleeps 6 in 3 bedrooms a few minutes walk from the yacht-filled harbour front in Cowes.

If you're looking for an inclusive English resort with eye-catching surroundings and activities galore, going with Palm Harbour in Cowes should be a foregone conclusion. Bring your whole family for a jolly good Isle of Wight seaside holiday. Pets welcome.

  • Sleeps 6
  • Bedrooms 3
  • Bathrooms 3

Self-catering holidays in Cowes would be incomplete without a trip to Osborne House, the magnificent family home of Queen Victoria, with opulent interiors, exotic plants and Victorian walled gardens. To delve into the town’s maritime history, visit the excellent Cowes Maritime Museum, on Beckford Road. In and around Cowes’ pedestrianised high street, you will find boutiques, gift shops and galleries. Cowes is also home to some of the Isle of Wight’s best restaurants. For a delicious evening meal, try award-winning Mojac’s Restaurant and Bar, renowned for its meat and fish dishes, prepared with local, seasonal ingredients. Murray’s is also a good option, with exceptional seafood, fresh from the local harbours.