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 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £257

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


West Flatlet is situated right in the heart of Seaview village and is perfect for couples looking for a coastal break. This small but cosy and comfortable first floor flat sits at ...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £257

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £272

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


This charming one bedroom apartment forms part of a country house, set around a shared Spanish-style courtyard, just outside the bustling village of Bembridge. You can enjoy the ev...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £272

We are Gold accredited with the Green Tourism Business Scheme.

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £286

1 bedroom self catering apartment near Ventnor, Isle of Wight


Sea Song is an attractive one bedroom, first floor apartment overlooking beautiful communal gardens and surrounded by woodland on the southernmost tip of the island. Perfect for ro...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £286

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £300

1 bedroom, rural self catering cottage in Newport, Isle of Wight


This absolutely gorgeous barn conversion is the perfect place for a couple's holiday, located on the Durton Farm Estate in the centre of the Island. Lovingly refurbished by the own...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £300

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £310

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


Located on the first floor of Shanklin Villa, a lovely Victorian property, this small studio apartment packs a punch despite its size. Enjoying beautiful sea views from its elevate...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £310

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £310

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


This contemporary studio apartment enjoys a great location in Shanklin. With modern decor and open plan living, it makes a cosy retreat for a couple looking for a coastal break. Wi...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £310

View
  • 20% off

    21 Dec 2018 - 28 Dec 2018

    £434.99 £348.00

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £348

1 bedroom self catering cottage near Ventnor, Isle of Wight


Located in a rural village setting, Berryl Mead View is a delightful home from home cottage with plenty of space, well equipped throughout and extremely comfortable living room wit...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £348

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

7 nights from £350

1 bedroom, dog friendly holiday cottage near the sea near Ventnor, Isle of Wight


This gorgeous barn conversion is set within the grounds of the stunning North Grounds Farm, just outside the village of Chale Green on the southern side of the Island. Laid over on...

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

7 nights from £350

We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £470

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


Sitting within a beautifully converted Victorian villa, The Cadogan Apartment offers a high standard of accommodation for a couple or lone traveller looking for a coastal break. Gu...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £470

View
  • 20% off

    20 Dec 2018 - 27 Dec 2018

    £659.97 £528.00

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

7 nights from £316

2 bedroom self catering cottage near the beach in Seaview.


Located in a small waterside development on the edge of Seaview, 62 Buddleia Cottage is a pretty beach bungalow offering comfortable accommodation, for a couple or small family, in...

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

7 nights from £316

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