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Isle of Wight Holiday Accommodation

Best of holiday homes and cottages to rent in IOW

Find Isle of Wight cheap accommodation and cottages

Find the best holiday rentals in the IOW by comparing prices and quality for exactly what you’re after for your trip to this edgy British island located in the English Channel with beaches and beautiful sand dunes to explore. Hundredrooms understand that it can be a difficult task to know exactly where to look to find the cheapest and best suited Isle of Wight holiday cottages. That is why we have created the technology to allow you to compare holiday apartments and houses from hundreds of site all at once. In a matter of seconds, you can see all of the available offers on on page and compare using the filters. Known as ‘England in Miniature’, the isle just 2 miles from the coast of Hampshire is separated by the Solent. Since the Victorian times, many holiday goers have chosen to book their holiday accommodation in the Isle of Wight and enjoy its 25 miles of coastline, and recently trendy atmosphere due to its surfing prowess and Isle of Wight Festival that takes over annually. From the comfort of a holiday letting, you can admire its dramatic cliffs, explore some of the oldest fossils found in Europe and find out more about its fascinating maritime tradition. Some even refer to it as ‘The Island’ - we can find you Isle of Wight holiday lettings for quick access to the likes of Portsmouth and Southampton. Looking for a cheap and quick getaway? We will show you what we have on offer for you to enjoy the vintage arcades and promenades alongside its iconic beaches. Experiencing a revival in recent years, this funky island has a milder climate than the English mainland, and so you should certainly consider a holiday home on the IOW.

Large holiday cottages

Dog-friendly holiday cottages

Holiday cottages for two

Best towns on the island

  • Newport: A historic town with many shopping facilities from high street shops to independent boutiques, and is considered to be the capital of the island. It is located inland and is very much the heart of the isle. Here you will find the site for the famous Isle of Wight Festival that takes place every June. The River Madina runs through the town and there are a great range of places to eat, alongside cafes. You will find some good self-catering accommodation here and is a good choice for your holiday in order to get around easily. It is a town characterised by gorgeous Victorian and Georgian architecture, and you’re sure to enjoy being located here.
  • Ryde: This is the largest of the towns on the island, and located at the beach, it is considered the gateway to the island. You can travel to and from various points on the mainland via catamaran and hovercraft, and there are a whole range of boutique shops and museums. Ryde is home to a Victorian 19th century pier that has been restored fully and is now an entertainment hub. Ryde also hosts a number of It has many offers for holiday accommodation as it is a popular seaside resort. You can find holiday cottages to rent and self-catering holiday homes. A viable option for nightlife, it is also home to a number of events such as the Isle of Wight carnival which is one of the oldest in the country.
  • Cowes: Home to the largest sailing regatta in the world, the Cowes Week event draws many to this town which is fantastic for sailing and water sports. It is a town that is divided in two by the River Medina, into East and West Cowes.
  • Sandown: Located in a gorgeous bay setting, it has a typical British pier and many entertainment attractions to choose from. You should head here for fossil hunting with the kids, alongside the Isle of Wight Zoo. It has a range of rental accommodation for you to enjoy.
  • Shanklin: Loved for its sandstone cliffs, this is a great option for a seaside resort. You can find many traditional beach huts and water sports facilities. There are a good range of holiday apartments and self-catering holiday lettings. Wile away the day by the Shanklin Esplanade, and unwind on the beach.
  • Ventnor: The island is considered to have its very own microclimate that meant in the Victorian times, it was a highly popular health retreat. It is a suntrap and has many beach huts. You can enjoy the local fish food and the traditional arcade. The Ventnor Botanic Gardens are particularly impressive; it is a subtropical paradise that you have to see.
  • Seaview: A village with incredible coastal views across the Solent. It is a popular place for booking a holiday cottage and is particularly great for its water sport facilities. You will be transported back in time by the decorous Edwardian architecture and shallow sands for glorious beach walks.

When to visit

In terms of picking a British holiday destination for guaranteed good weather, Isle of Wight claims to have the best weather in the whole country. So naturally, booking a self-catering cottage in the summer months is preferable if you don’t want the risk of drizzling and wet weather. The warmest months are naturally July and August, and rainfall is somewhat lower between May and August. However, prices for holiday cottages are cheapest in spring and autumn - March to May, and September to October. The price for holiday accommodation is also higher during the Isle of Wight Festival in June, or Cowes Week in August (unless you have a yacht!) Given that it is an island, the roads can get quite busy during the summer months, so for peace and quiet and cheaper prices in holiday rentals, we suggest spring and summer.

Alum Bay and other points of interest

  • Blackgang Chine:The world’s oldest theme park, it was formerly a gorge through to the sea. It collapsed some years ago, but the theme park is still like stepping back in time and merits a visit.
  • Ventnor Botanic Garden: A botanic garden with a subtropical climate that has various flora grown in both the Mediterranean and mainland Britain.
  • Osborne House: The former royal residence of Queen Victoria, as her family home.
  • Carisbrooke Castle: A motte and bailey castle that was built in the 12th century. It is a former Elizabethan fortress, a prison and a royal residence. Its history is certainly worth discovering.
  • Isle of Wight Steam Railway: A heritage railway that passes through the countryside on the island. It has many Victorian and Edwardian carriages.
  • The Needles: An iconic stack of chalk rocks that rise out of the sea near Alum Bay. You can take a chairlift to see these natural wonders.
  • Steephill Cove: This cove can only be reached on foot, and has a delicious seafood restaurant looking out over the sea. The crabs and lobster are fresh as you can get!
  • Alum Bay: A famous bay which is best known for its multicoloured sand on the beach that appears naturally and can be kept as a souvenir in a glass paperweight.