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 135 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

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

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £462

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


4A Ship House, an attractive townhouse positioned right in the middle of Seaview, is perfect for a family looking for a coastal break. 'Ship shape' in presentation, the fantastic t...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £462

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  • 50% off

    29 Mar 2019 - 5 Apr 2019

    £405.31 £202.50

  • 25% off

    5 Apr 2019 - 12 Apr 2019

    £528.45 £396.00

  • Sleeps 5 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £474

2 bedroom, dog friendly holiday apartment near the beach in Shanklin.


Park Lodge Annexe is a beautifully presented lower ground floor apartment within walking distance to the Rylstone Gardens and the Chine. The cliff path is a minute stroll away, lea...

  • Sleeps 5 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £474

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £508

3 bedroom self catering apartment with sea views in Seaview, Isle of wight.


Elm Cottage is a stylish first floor apartment brimming with character and comfort. It would suit friends traveling together, a couple or a family. From the front courtyard to t...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £508

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  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £450.84 £360.67

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £520

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


This charming first floor apartment is laid over two floors and situated right in the heart of Seaview village, tucked away down a quiet side street called Rope Walk, so called as ...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £520

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £560

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


The location of 40 Trelawny Way, on a quiet residential road in Bembridge, belies its extravagant interior. For those looking for a family home with an interior decorated with arti...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £560

View
  • 20% off

    30 Mar 2019 - 6 Apr 2019

    £516.97 £413.58

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £709

3 bedroom self catering apartment near the beach in Seaview, Isle of Wight


An incredibly stylish three bedroom ground floor apartment ideally located a few minutes' walk from the village of Seaview and the beach. A lovely large entrance hall centrally fra...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £709

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

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £725

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


A very charming house overlooking The Green in the picturesque village of St Helens, on the east side of the Island, within a short and scenic walk to the beach. A footpath startin...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £725

  • Sleeps 5
  • Regret no pets
  • Changeover Sat

7 nights from £781

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


Dating back to 1863 and converted in 2011, this superb two-storey apartment is located on the outskirts of Shanklin. 10 Shanklin Manor has an elegant, monochrome interior and the u...

  • Sleeps 5
  • Regret no pets
  • Changeover Sat

7 nights from £781

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  • 10% off

    30 Mar 2019 - 6 Apr 2019

    £676.52 £608.87

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £425

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


Located in a quiet side street just off the village green in St Helens, this cosy cottage offers great accommodation with a good sized garden, spacious decking and outdoor seating ...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £425

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £492

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


10 Tollgate Cottages is a pastel coloured, beach bungalow set in a small gated development close to the waterfront. Clean, neutral decor and its close proximity to the beach make t...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £492

View
  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £431.72 £345.37

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