The Isle of Wight, England’s largest island, is an extremely popular self-catering holiday destination for those looking to stay in the UK. This is due to its warmer climate, golden sand beaches, superb sailing and notable events such as Cowes Week and the Isle of Wight Festival in Newport. Food festivals, jazz festivals and outdoor concerts also regularly take place on the island. Travel to the Island by car of passenger ferry from Lymington, Portsmouth or Southampton on companies such as Wight Link. For a more peaceful experience, experience, pedal the many idyllic cycle paths that have recently given the Isle of Wight the status as one of the top cycling destinations in the world, with over 500 miles of cycle tracks. Relax in quaint Victorian resorts - now much restored, such as Yarmouth, Ventnor and Freshwater.

53 cottages found 53 match all criteria.

Families are spoilt with elegance at Hampton House, a luxury cottage with views of picturesque Freshwater beach on the Isle of Wight. The pet-friendly property offers contemporary chic and natural light throughout its five bedrooms and its extensive living space, which includes a log burning fire.

House on the Beach is a fantastic large Isle of Wight coastal cottage offering absolute beach frontage and magnificent views over a beautiful stretch of private beach at Fishbourne. The luxury property has 6 bedrooms and a generous deck which is made for relaxing holidays and special occasions.

Waterfront Retreat in the Isle of Wight sailing resort of Yarmouth is a 2-bedroom holiday cottage. It is stylish decorated and furnished to create a sense of relaxation using driftwood ornaments and calming seaside colours for 2-4 guests (snd red squirrels living at the bottom of the garden).

An Isle of Wight rural retreat in the little hamlet of Wooton Bridge, Shiloh Cottage offers self-catering holidays in a farm cottage with panoramic countryside views. With walks from the door and the coast at Ryde within a 10-minute drive it’s a peaceful location from which to explore the Island.

Rush House is a large, luxurious and pet friendly Isle of Wight holiday cottage with a hot tub sleeping 20 guests in 8 bedrooms near the seaside resort of Shanklin. It welcomes large families or groups of friends for traditional holidays, anniversaries and reunions.

The seven double bedroom Gladices Barn is a large Isle of Wight holiday cottage with a hot tub and fine rural views on a farm above Clyffe Pypard. The use of a very efficient Geo-thermal heating system heats the floors, to create a warm and cosy holiday cosy holiday cottage at any time of the year.

Northcourt House is a large Isle of Wight holiday home on the edge of the picturesque village of Shorwell. This pet friendly Grade II-listed Jacobean Manor House set in 15-acres of rural splendour offers sublime group accommodation for 36 guests in 2 wings of the Manor.

  • Sleeps 36
  • Bedrooms 16
  • Bathrooms 15

Standing in a rural village location on the Isle of Wight near the beaches at Sandown, Esher is a large, spacious holiday cottage with a swimming pool that sleeps 8 in 4 bedrooms. This child friendly country house with panoramic views, has woodland and riverside walks from the front door.

A family- and pet-friendly country getaway filled with rustic charm and modern amenities. Convenient to the coastline and many popular Isle of Wight resort of Ryde, Little Duxmore Barn has everything for a luxury self-catering holiday in a detached cosy, private package.

  • Sleeps 8
  • Bedrooms 4
  • Bathrooms 2

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.

Fancy a lighthouse holiday? Book Gunard, a Ventnor holiday cottage, part of St Catherine's Lighthouse on the Isle of Wight. With superb sea views, this pet-friendly waterside cottage sleeps 5 in a secluded rural location.

Olive is an open plan luxury eco-hut for couples in a peaceful rural location in the Isle of Wight near Wootton. Nestling within a private gated residence, it is guaranteed to fulfil any couple’s desires for peace and quiet away from the commotion of day to day life.

A few miles inland from the coast at Cowes, Hill Top Cottage is a beautiful barn conversion in quiet rural surroundings on the Isle of Wight. The pet friendly Island holiday cottage offers self-catering holidays for families and friends. It sleeps 6 guests in two bedrooms.

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.

Relax in style at Oak Cliff Villa, a luxury Victorian house with a pool on the Isle of Wight in Wootton offers uninterrupted sea views over the Solent to Portsmouth. This large, light and spacious, holiday cottage is set in five acres of grounds and sleeps 16.

With fourteen bedrooms and ten baths, Shalfleet is a large Isle of Wight holiday home comprising a breathtakingly restored manor house, a cottage, a farmhouse, a barn and swimming pool near the coastal resort of Newport. Pets welcome.

With fourteen bedrooms and ten baths, Shalfleet is a large Isle of Wight holiday home comprising a breathtakingly restored manor house, a cottage, a farmhouse, a barn and swimming pool near the coastal resort of Newport. Pets welcome.

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

North House is a magnificent Grade II listed waterside holiday cottage in Yarmouth on the Isle of Wight, ideal for special occasions. The large, 7-bedroom seaside house includes antique furnishings, stunning views, a spacious garden with room for pets and modern comforts as well as two open fires.

The Bouldner is a large Isle of Wight Holiday Cottage in Yarmouth with beautiful sea views across the Solent. This pet-friendly, 5-bedroom cottage, sleeps 10 in 5 bedrooms and welcomes large or extended families or friends for summer holidays on the Island or short breaks at other times.

West Winnowing is a holiday cottage near Ventnor on the Isle of Wight in the peaceful coastal village of Niton with spectacular sea views over the island's coastline. Set within an Area of Outstanding Natural Beauty, this luxury coastal cottage sleeps 5. Pets welcome.

Mill Reach is a stylish 2-bedroom holiday let a short stroll from the River Yar in Yarmouth, a picturesque seaisde town on the Isle of Wight with views across the Solent. Perfect for 2-4 guests seeking a long holiday or short break by the sea in an Area of Outstanding Natural Beauty.

La Belle Vie is a large country house with a hot tub and games room offering luxury self-catering holidays for up to 12 guests in Godshall on the Isle of Wight. Standing near Ventnor and Shanklin in 3-acres of grounds, this pet friendly house is furnished to a satisfyingly high standard.

The Isle of Wight has a constant programme of events and is home to some of the biggest festivals in England. The music festivals; The Isle of Wight Festival and Bestival, draw in huge crowds and famous artists year after year during the summer period. If music isn’t your thing the Isle of Wight Walking Festival, currently the biggest in the UK, takes place in Easter where you might just find some incredible walking routes that are hidden away from society. After a hard day’s walk, what can be better than to return to the comfort of a well equipped self-catering cottage and luxuriate in a hot bath or shower.

Two major English historical characters made their home here - the Poet Laureate, Alfred Lord Tennyson and Queen Victoria whose final home was Osborne House at East Cowes. The house and gardens have been beautifully preserved and are open to viewers daily.

The Isle of Wight is also renowned as one of the richest areas for Dinosaur discovery in Europe, which has subsequently earned it the title “Dinosaur Island”. This history has meant that some of the best Dinosaur museums are on the Isle of Wight, including the award winning Dinosaur Isle. You can even get involved with fossil hunts where you can discover your own fossils, ideal for a family day out. If you’re looking for something more adventurous for your holiday, you can paraglide, race around in land yachts along the golden sands or go-kart across the all-weather track at Wight Karting.

Being surrounded by the English Channel and separated from the mainland by the Solent means that there is a great opportunity for some incredible beaches across the 57 miles of coastline. Over 17 of them have blue flag and seaside awards in 2013 – more than any other destination in England. With miles of award winning sand and shingle beaches, rugged cliffs, hidden coves and clear waters, a trip to the beach is an essential part of any visit to the Island. Water sports are also particularly popular, and there are endless places to hire surfing equipment or kayaks. The first hovercraft was developed on the island, so for a truly unique experience hop on the Hovertravel, Isle of Wight’s Hovercraft service between the Island and Portsmouth.