Cottages for October Half Term on the Isle of Wight

Pack your bags and round up the kids, an autumn holiday on the Isle of Wight is beckoning. Giving you something special to look forward to this October half term, all of our Isle of Wight cottages perfectly combine homely touches with modern luxuries. Take a look through our collection and find the one just right for you. The holiday of a lifetime is but moments away. Read more

A holiday on the Isle of Wight provides stunning coast, beautiful countryside and lots to see and do. With October often hanging onto good weather post-summer, it is a great time to explore the island and take in the sights. Making the most of the daylight hours before nights draw in and book yourselves a luxurious break on the Isle of Wight. Even if the weather takes a turn for the worse, stormy days can be hugely atmospheric, particularly if you have a sea view cottage on the Isle of Wight. As well as a complete inventory, many of our cottages offer unique facilities too, like games rooms and wood burners, so you can enjoy a break from the rhythm of everyday life in total comfort and style. Look through our 151 cottages available for October half term and find your favourite one.

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

151 luxury cottages for October half term on the Isle of Wight

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £457

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


A barn conversion in a rural setting, you'll enjoy a feeling of peace from the moment you step inside this lovely retreat, with its exposed beams and rustic decor. Sitting within t...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £457

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £457

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


A barn conversion, in a rural setting, with a welcoming, rustic feel to it, 1 Bagwich Barn offers an ideal base in the middle of the The Isle of Wight, from which to explore north ...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £457

We’ve been raising the standards of self catering holidays since 1977.

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

7 nights from £460

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 £460

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £464

2 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight


Originally the farms milking parlour, Dairy Cottage is a light and airy ground floor cottage with plenty of charm throughout. With a double bedroom with pleasant views across the f...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £464

View
  • 20% off

    21 Dec 2018 - 28 Dec 2018

    £549.00 £439.20

  • 20% off

    28 Dec 2018 - 4 Jan 2019

    £549.00 £439.20

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £464

2 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight


Originally the farm's milking parlour, this delightful cottage sleeping four is the perfect cottage to spend quality time together as a family in a stunning rural location. Located...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £464

View
  • 20% off

    21 Dec 2018 - 28 Dec 2018

    £549.00 £439.20

  • 20% off

    28 Dec 2018 - 4 Jan 2019

    £549.00 £439.20

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

7 nights from £470

2 bedroom thatched self catering cottage with sea views in Seaview.


If the restorative power of the sea appeals to you, 1 Thatched Cottage, with its uninterrupted views is an ideal holiday home. This 19th century property combines old world charm w...

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

7 nights from £470

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

7 nights from £472

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


Located in the cosmopolitan town of Ventnor in a Victorian town house, Seascape is a modern two bedroom apartment with spectacular sea views along the coastline. It offers contempo...

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

7 nights from £472

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

7 nights from £480

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 £480

View
  • 10% off

    29 Dec 2018 - 5 Jan 2019

    £694.98 £625.50

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.

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

7 nights from £481

2 bedroom self catering cottage near the beach in St Helens, Isle of Wight.


Fir Cottage is an attractive and contemporary conversion of a Victorian home, located right in the heart of St Helens. The village green (England's second largest) lies a few yards...

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

7 nights from £481

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

7 nights from £484

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


If you're looking for a property that's practically on the beach, then this is it! 1 Starboard House perches just opposite the beach in central Seaview and enjoys uninterrupted sea...

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

7 nights from £484

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