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 92 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

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

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £301

1 bedroom self catering cottage near Ventnor, Isle of Wight


Located in a rural village setting, Berryl Mead View is a delightful home from home cottage with plenty of space, well equipped throughout and extremely comfortable living room wit...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £301

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £360

1 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.


Sitting within a beautifully converted Victorian villa, The Cadogan Apartment offers a high standard of accommodation for a couple or lone traveller looking for a coastal break. Gu...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £360

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

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £316

2 bedroom self catering cottage near the beach in Seaview.


Located in a small waterside development on the edge of Seaview, 62 Buddleia Cottage is a pretty beach bungalow offering comfortable accommodation, for a couple or small family, in...

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £316

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £435

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


This beautifully refurbished house is perfectly situated in the heart of Seaview Village, with a lovely decked area to the rear and outdoor seating so you can enjoy dining in the I...

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £435

  • 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
  • Regret no pets
  • Changeover Fri

7 nights from £301

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


The Crows Nest is a second floor apartment at the top of a Victorian property in the historic village of Seaview. A family looking for a convenient base from which to enjoy the Isl...

  • Sleeps 4 + cot
  • Regret no pets
  • 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 bolthole 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 b...

  • 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 £319

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


The Lobster Pot is a comfortably furnished beach bungalow located in a small waterside development on the edge of Seaview and next to a nature reserve. This beach bolt hole has dec...

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

7 nights from £319

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

  • 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

View
  • 25% off

    15 Dec 2019 - 20 Dec 2019

    £262.40 £196.80

  • 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

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