Holiday Cottages with Wifi on the Isle of Wight

Pack your bags and head to the Isle of Wight. We have a range of 157 self-catering holiday cottages with Wifi primed and ready to welcome you. Stay up-to-date with all the latest news, events and reports and enjoy a slice of luxury. Each of our properties on the Isle of Wight has been personally inspected and fully equipped so your holiday is the best it can be. Read more

With so many attractions and events taking place across the Isle of Wight, the internet can be an excellent source of up-to-date information and news. Surf the net from the comfort of your home-from-home and stay in touch with friends and family, sharing pictures and anecdotes. At Classic Cottages we have a selection of 157 self-catering retreats with Wifi primed and ready for you. From rural retreats to sea view cottages to town hubs, you are sure to find the cottage of your dreams on the Isle of Wight. 

Cottages with Wifi on the Isle of Wight

Whether you are looking forward to a solo retreat, a family-friendly property or a spacious cottage for a group gathering with friends, our cottages with Wifi come in all shapes and sizes. It's great news if there is a four-legged member of your tribe too, as many of our cottages are dog-friendly. Priding ourselves on marketing the finest quality self-catering accommodation on the Isle of Wight, we handpick and personally inspect each cottage, making sure each is fully equipped with a complete inventory. Secure your dream holiday and book your favourite cottage today. 

Isle of Wight Ferry Booking With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing

157 Isle of Wight cottages with Wifi

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £301

2 bedroom, rural self catering cottage near the beach in Bembridge, Isle of Wight.


Take a few steps up to the entrance and you will find yourself in 3 Kings House, a ground floor apartment in a small development. It is the perfect base for a couple or a family wi...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £301

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £301

2 bedroom, dog friendly apartment near the beach in Bembridge, Isle of Wight.


This two bedroom apartment in Bembridge is small but perfectly formed. Lovingly restored by the owners, 53a offers a perfect base for a family with a light and airy double bedroom ...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £301

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £316

2 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.


The perfect bolt-hole for families, 61 Drake Cottage is a comfortably furnished beach bungalow located in a small waterside development on the edge of Seaview. Just yards from the ...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £316

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £328

2 bedroom, dog-friendly holiday cottage with sea views in East Cowes, Isle of Wight


Smugglers' Run is a waterside property overlooking the River Medina and across to the sailing town of Cowes. It would suit a family or a couple in need of a little extra space. ...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £328

Need more time? Reserve any cottage for up to 24 hours before booking.

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £340

2 bedroom, dog friendly holiday cottage near the beach in St Helens, Isle of Wight.


Faithfull Cottage is a lovingly restored, pretty mid-terrace cottage which enjoys a rear garden and countryside views on the outskirts of St Helens. This comfortable cottage is set...

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £340

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £350

2 bedroom self catering apartment with sea views in Ventnor, Isle of Wight


With one of the best views on the Isle of Wight, 1 St Josephs is a superb ground floor apartment beautifully decorated throughout. The property has a large patio area spanning two ...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £350

  • Sleeps 4 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £352

2 bedroom self catering apartment with sea views in Ventnor, Isle of Wight


6 St Joseph’s has stunning panoramic sea views, which you can sit and admire from the balcony, living room and master bedroom! Ideally positioned between Bonchurch and Ventnor this...

  • Sleeps 4 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £352

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £354

2 bedroom, rural self catering cottage near the beach in Seaview, Isle of Wight.


Yardley is a charming Victorian cottage, set in the centre of the pretty sailing village of Seaview. The beach and local shops are only a few minutes from your doorstep making this...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £354

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £357

2 bedroom, rural self catering cottage near the beach in Brighstone, Isle of Wight


One of two beautifully converted barns right in the heart of the Island's Area of Outstanding Natural Beauty. Equipped and decorated to a high standard mixing the charming features...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £357

  • Sleeps 4 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £357

2 bedroom, rural self catering cottage near the beach in Brighstone, Isle of Wight


Nestled in the stunning countryside on the south west coast of the Island with far reaching sea views over the Military Road, this gorgeously converted barn is the perfect holiday ...

  • Sleeps 4 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £357

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