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 149 available cottages to find your perfect one, or get in touch for more information. 

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149 self-catering cottages on the Isle of Wight

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

7 nights from £750

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


A spacious family home, 17 Sandcove Rise is located on a quiet cul-de-sac in the pretty village of Seaview. It would suit a large family or several couples or friends traveling tog...

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

7 nights from £750

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  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £750.06 £600.05

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

7 nights from £750

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


House of Logs is a unique and stunning property located on the west coast of the Island, just a short walk from Widdick Chine and Totland Bay. Perfect for a peaceful holiday, the h...

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

7 nights from £750

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

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

7 nights from £781

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


Spread over three floors The Swallows really is a beautiful family holiday home. The ground floor is very fresh, light and modern and has bi-folding doors leading out onto the pati...

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

7 nights from £781

View
  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £885.07 £708.06

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £799

4 bedroom self catering cottage in Godshill, Isle of Wight


Nestled in the heart of the chocolate-box village of Godshill, this detached house has beautiful secluded gardens to the rear and everything the village can offer within a few minu...

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £799

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £841

4 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight


With stunning sea views from not one but two balconies Solent View Road is a wonderful holiday destination within a few minutes' walk from Seagrove Bay. Located just on the outskir...

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £841

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £850

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


This completely refurbished cottage is nestled at the end of Ryde Road, just a short walk from the beach and Seaview village. With off-street parking and a lovely large garden to t...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £850

View
  • 15% off

    22 Mar 2019 - 29 Mar 2019

    £974.98 £828.73

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

7 nights from £850

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 minutes walk to the beach and Bembridge village. There is a spacious kitchen/diner with doors o...

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

7 nights from £850

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

7 nights from £852

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

7 nights from £852

View
  • 20% off

    5 Apr 2019 - 12 Apr 2019

    £1524.96 £1219.97

We’ve been raising the standards of self catering holidays since 1977.

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

7 nights from £867

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

7 nights from £867

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

7 nights from £925

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


Set within a converted Victorian villa, Eversley Apartment is a large, contemporary split level apartment. With modern furnishings, this property offers a luxury option for a coast...

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

7 nights from £925

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