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 154 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

154 self-catering cottages on the Isle of Wight

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


The wow factor at 4 Commodores Court is the location; perched directly opposite the beach it has stunning views of the Solent from the front, and delightful rural and lakeside view...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £470 - £571

3 bedroom self catering apartment near the beach in Seaview.


A ground floor apartment housed within an exclusive development, you'll feel an air of grandeur to a holiday at 3 Springfield Court. We're not ones to use the 'stunning' descriptor...

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

Price per week £480 - £677

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


If it is beach access and sea views you want, then it is difficult to beat Merries. The traditional beachside bungalow offers simple, comfortable accommodation with a large rear ga...

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

Price per week £480 - £710

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


A fabulous holiday home, Trevenna is contemporary in style and many thoughtful touches are provided for guests. The interior is clean and fresh, there are wooden floors throughout ...

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

Price per week £481 - £742

3 bedroom self catering apartment with sea views in Seaview.


They say location is everything, and this property does not disappoint! Situated on the first floor, 2 Quay Rocks is a light-filled, modestly furnished apartment with a balcony, of...

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

Price per week £490 - £643

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


This gorgeous property is a stylishly converted coastguard cottage and really is a gem. Beautifully decorated throughout, in greys, blues and whites, it is an oasis of calm and has...

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

Price per week £493 - £694

Our guests rate us 4.8/5 on Feefo, the independent review site.

3 bedroom self catering cottage with sea views in Cowes, Isle of Wight.


Right in the heart of the bustling sailing town of Cowes, 9 Crown Court offers great accommodation with a stunning roof terrace boasting uninterrupted views across the rooftops to ...

  • Sleeps 6
  • Regret no pets
  • Changeover Sat

Price per week £500 - £725

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


Welcome to Solent Peek, a lovely comfortable home in Totland on the West Coast of the Island. As the name suggests, there is sea view from the first floor master bedroom and it is ...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £505 - £709

3 bedroom self catering cottage in East Cowes, Isle of Wight


Turnstone is a beautifully designed, newly built town house situated overlooking the River Medina on the north coast of the island and within walking distance of Osborne House. Fro...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Sat

Price per week £505 - £653

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


This charming cottage is tucked away down an unmade road just off Bembridge Harbour, within walking distance of Bembridge village centre. The front and rear gardens of Old Railway ...

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

Price per week £505 - £729

Loading more