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 159 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

159 self-catering cottages on the Isle of Wight

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


Walnut Cottage is a real find if you're looking for a spot of luxury on holiday. Tucked away in central Seaview village Walnut offers spacious accommodation over two floors and an ...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

Price per week £835 - £1495

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  • 20% off

    19 Oct 2018 - 26 Oct 2018

    £1494.99 £1195.99

4 bedroom self catering cottage with sea views in Seaview, Isle of Wight


Tides Reach is a wonderful, newly modernised family house along the Seaview Duver just a short walk into Seaview Village and the Yacht Club. Tides Reach has a stylish open plan sit...

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

Price per week £850 - £1075

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


A wonderful contemporary beach house, offering accommodation for eight, within a few minute's walk to the beach and Bembridge village. There is a spacious kitchen/diner with doors ...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

Price per week £850 - £1275

4 bedroom converted barn with far reaching rural views in St Helens, Isle of Wight.


Hill Farm Barn is an immaculately presented and impressively converted 18th Century Threshing Barn standing in half acre of private grounds. Perched on a hilltop half a mile from a...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

Price per week £995 - £1370

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


This pretty attached Victorian cottage sits in the grounds of the Priory Estate and comes with use of its many diversions. With 70 acres of grounds to explore, plus a stunning priv...

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £1013 - £1530

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  • 20% off

    19 Oct 2018 - 26 Oct 2018

    £1530.24 £1224.19

4 bedroom self catering cottage with sea views in Seaview, Isle of Wight


A spectacular waterfront three-storey house situated on Seaview duver with uninterrupted sea views from the kitchen/dining-room and the first floor balcony. Just a few steps from y...

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

Price per week £1100 - £1600

4 bedroom, rural self catering cottage near the beach in Yarmouth, Isle of Wight


This beautiful house is set in several acres of garden on the outskirts of Yarmouth, just a few minutes walk to the water’s edge, a truly stunning holiday destination. The property...

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

Price per week £1375 - £2000

4 bedroom, rural self catering cottage with estuary views near Newport, Isle of Wight


This superb property overlooks the River Medina from its corner plot in the exclusive Island Harbour development. Laid over four storeys offering stunning views across the River Me...

  • Sleeps 8
  • Regret no pets
  • Changeover Sat

Price per week £1400 - £1950

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


6 Seafield Terrace is a charming terraced cottage set in the pretty village of Seaview. With spacious accommodation spread over three floors, and the beach close at hand, it makes ...

  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £647 - £825

5 bedroom self catering cottage near the beach in Ryde, Isle of Wight.


Middle Lodge is a gorgeous 1860s, stone-built, Victorian holiday home set in a mature enclosed garden on the edge of Ryde on the east of the island. The outside is charmingly perio...

  • Sleeps 9 + cot
  • Regret no pets
  • Changeover Sat

Price per week £704 - £1089

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  • 15% off

    19 Oct 2018 - 26 Oct 2018

    £1088.67 £925.37

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

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