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 83 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

83 self-catering cottages on the Isle of Wight

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

7 nights from £287

Mariners Cove

3628

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 th...

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

7 nights from £287

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

7 nights from £357

Berryl Mead View

3906

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. It is well-equipped throughout and has an extremely comfortable li...

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

7 nights from £357

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

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

7 nights from £505

The Cadogan Apartment

3667

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 £505

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

7 nights from £316

62 Buddleia Cottage

3566

2 bedroom self catering cottage near the beach in Seaview.


Located in a small waterside development in a quiet corner away from the road on the edge of Seaview, 62 Buddleia Cottage is a pretty beach bungalow offering comfortable accommodat...

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

7 nights from £316

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £479

The Cattle Byre

4535

2 bedroom, dog friendly self catering cottage near Brighstone.


The Cattle Byre has accommodation for three guests across two bedrooms, a double and a single. It has two private outdoor seating areas, the rear enclosed garden can only be access...

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £479

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

7 nights from £505

The Worsley Apartment

3682

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


Offering a high standard of accommodation, The Worsley Apartment is a ground floor apartment within Shanklin Villa, a beautifully converted Victorian building. With a separate kitc...

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

7 nights from £505

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

7 nights from £316

61 Drake Cottage

3565

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


The perfect bolthole for families in a quiet corner away from the road, 61 Drake Cottage is a comfortably furnished beach bungalow located in a small waterside development on the e...

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

7 nights from £316

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

7 nights from £319

The Lobster Pot

3672

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


The Lobster Pot is a comfortably furnished beach bungalow located in a small waterside development on the edge of Seaview and next to a nature reserve. This beach bolt hole has dec...

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

7 nights from £319

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

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

7 nights from £328

Cockleshells

3815

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 accommodation offers a double...

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

7 nights from £328

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

7 nights from £357

6 Pier View Court

3559

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

7 nights from £357

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