Holiday Cottages for October on the Isle of Wight

Although you may not expect it to be so, the Isle of Wight often benefits from lots of sunshine and mild weather well into October. With the sea warmed from months of the sun's rays and the atmosphere calm, it is a truly wonderful time of year to explore the island. Book a luxury retreat and enjoy the island from a home-from-home this October.Read more

Rolling countryside bearing colours of rust, deep red and burnt orange, long sandy beaches bathed in warm sunshine and quiet towns and promenades: this is October on the Isle of Wight. However you'd like to spend your holiday and whoever you'd like to share it with, the Isle of Wight offers a beautiful playground where adventure beckons. With as many opportunities to relax as to explore, you can spend your days exactly as you please and return to your own slice of paradise. At Classic Cottages, we pride ourselves on marketing only the highest quality self-catering accommodation around.  Handpicking and personally inspecting each property, we make sure each meets exacting standards so your whole holiday is the best it can be. Browse our 156 available cottages to find your perfect one, or get in touch for more information. 

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

156 self-catering cottages on the Isle of Wight

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

7 nights from £470

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


Offering a high standard of accommodation, the Worsley Apartment is a ground floor apartment housed within Shanklin Villa, a beautifully converted Victorian building. With a separa...

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

7 nights from £470

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £290

2 bedroom self catering cottage near the beach in Seaview.


This delightful, stylish seafront bungalow is located in a front row position with wonderful views of the Solent and the beach is practically on the doorstep. Days at the seaside, ...

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £290

View
  • 15% off

    1 Mar 2019 - 8 Mar 2019

    £289.98 £246.50

  • 15% off

    8 Mar 2019 - 15 Mar 2019

    £289.98 £246.50

  • 15% off

    15 Mar 2019 - 22 Mar 2019

    £289.98 £246.50

  • 15% off

    22 Mar 2019 - 29 Mar 2019

    £352.56 £300.05

  • 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

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

  • 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 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 £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

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

7 nights from £320

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


Cockleshells is one of the charming Salterns bungalows situated along the Seaview Duver within a short walk to the Yacht Club and Seaview Village. The new Owner has completely rede...

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

7 nights from £320

  • 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
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £344

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 £344

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