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.

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 158 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

158 self-catering cottages on the Isle of Wight

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


With an interesting history and dating from 1852, Trevessa was once a fishing cottage and overlooks the sea. The sitting-room, dining-room and both bedrooms have beautiful sea view...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £314 - £612

View
  • 25% off

    19 Oct 2018 - 26 Oct 2018

    £611.62 £458.71

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

Price per week £314 - £450

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

Price per week £318 - £457

2 bedroom self catering apartment near the beach in Seaview.


A spacious, stylish, ground floor apartment in the sought-after Springfield Court complex, Apartment 4 offers guests the shared use of eight acres of mature landscaped grounds, a t...

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

Price per week £326 - £517

View
  • 20% off

    20 Oct 2018 - 27 Oct 2018

    £517.10 £413.68

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

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


Lapwing Cottage is a comfortable and neatly presented holiday bungalow located on the edge of the Salterns Holiday Village, in the charming village of Seaview. There are on site am...

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

Price per week £329 - £579

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


Little Egret Cottage is a comfortable, modest holiday bungalow set within a small development of similar properties on the edge of the Salterns Holiday Village. The bungalow has an...

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

Price per week £329 - £579

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


Kitty Wake is a comfortable and neatly presented holiday bungalow located on the edge of the Salterns Holiday Village, in the charming village of Seaview. There are on site ameniti...

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

Price per week £329 - £579

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


Wagtail is a comfortable and neatly presented holiday bungalow located on the edge of the Salterns Holiday Village, in the charming village of Seaview. There are on site amenities ...

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

Price per week £329 - £579

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. Watch the boats sail by from the privacy of the balcony off the living-...

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

Price per week £337 - £441

2 bedroom self catering apartment near the beach in Ryde.


6 Pier View Court, perfectly located right on the seafront at Ryde, is a modern, well presented second floor apartment, tastefully decorated and furnished to a high standard. Relax...

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

Price per week £344 - £479

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

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