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 152 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

152 self-catering cottages on the Isle of Wight

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £860

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


This is a three-storey house right in the heart of Bembridge village, just opposite the picturesque village church and a few minutes' walk from the shops and restaurants. The prope...

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £860

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1302

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


This impressive 150 year old Farmhouse sleeps nine and is the perfect location for a fabulous family gathering of all ages. In the breathtaking location of Barton Manor Estate, adj...

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1302

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £732

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


Orchard House is a wonderful property for an extended family looking for a sprawling holiday home near the beach in Bembridge. The downstairs living areas are inviting - no doubt t...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £732

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £753

5 bedroom, dog friendly holiday cottage with sea views in Wootton, Isle of Wight.


Creekside is a fabulous waterfront property that makes a wonderful choice of holiday home at any time of the year. This stunning detached house, set on the banks of Wootton Creek, ...

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £753

View
  • 15% off

    22 Mar 2019 - 29 Mar 2019

    £822.82 £699.40

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £891

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


Mariners is a beautiful beachfront property offering light, spacious, contemporary family accommodation. Tastefully refurbished in recent years, this modern property is spread acro...

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £891

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £893

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


Swift Cottage is a gorgeous, comfortable Edwardian end-of-terrace property, spread over three levels with wooden flooring throughout the kitchen and dining area. The spacious dinin...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £893

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

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1009

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


Seacrest House is a stunning holiday home with fabulous Solent views across beautiful Appley beach and is perfect for a large family or group of friends looking for a property with...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1009

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1200

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


This stunning converted coach house, benefitting from a fabulous location within the grounds of the Priory Estate, is an exceptional holiday home-from-home. The Priory Coach House ...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1200

View
  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £1199.80 £959.84

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1269

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


A wonderfully modern property, beautifully furnished and housed in an American-style cladded exterior, Pitt Corner is roomy, with plenty of space for the family to spread out. As w...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1269

View
  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £1348.48 £1078.78

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1658

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


A truly amazing, contemporary home with views directly out to sea, in the popular sailing town of Cowes. Offering exceptional quality throughout the whole home this is a superb bas...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1658

Loading more