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 142 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

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

  • 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

  • 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

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

  • 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

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £468

3 Astra House is a comfortable first floor apartment within a converted Victorian House


3 Astra House is a comfortable first floor apartment within a converted, red brick Victorian house, located on a quiet residential no-through road in Seaview. Offering light and sp...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £468

  • 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.


27 Tollgate Cottages is one of a number of well presented, beachfront holiday bungalows situated in Salterns Village, a small gated development located opposite Seaview Duver and b...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £492

  • 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.


6 Tollgate Cottages is a bright and cheery cottage set in a small, gated development near the pretty village of Seaview. Close to the beach, local shops and bars, and with Cafe Blu...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £492

  • 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

  • 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


24 Tollgate Cottages is a comfortable property just a stone's throw away from the beach, and a short walk from the local shops and dining in Seaview village. Situated on a small de...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £492

Choose from our exclusive collection at the best prices with real time availability.

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £509

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


30 Seaview Bay is a lovely three bedroom apartment set over two levels, offering sea views from the master bedroom balcony. Doors from the sitting-room lead to a decked area and pr...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £509

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £514

3 bedroom self catering cottage near the beach in Shanklin.


25 Palmerston Road is a bright, cheerfully decorated, family home and is one of our most popular properties. This property is a real find for a family looking for a home both close...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £514

Loading more