Holiday cottages for October on the Isle of Wight

Booking an Isle of Wight holiday cottage in October sounds more like a winter break, but the summer can be extended by a few extra weeks down here. 

We’re not promising, but you could be on the beach enjoying the best the Isle of Wight has to offer. And at this time of year you can also bring the dog and the sea is still warm, well fairly! If stormy seas don’t float your boat, it is a great time to explore the many gardens and woodlands in the area as they put on golden autumnal coats for their end of year display. Bring the family  to relive memories of a spent summer or indulge in a luxury short break before the winter kicks in. We have 180 holiday cottages for October on the Isle of Wight for you to choose from.

Isle of Wight Ferry Booking With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing

180 Self Catering Cottages on the Isle of Wight

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

Price per week £309 - £444

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 housed within Shanklin Villa, a beautifully converted Victorian building. With a separa...

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

Price per week £360 - £470

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


Take a few steps up to the entrance, and you'll find yourself in 3 Kings House, a ground floor apartment in a small development. The property is just a short walk from Bembridge Ha...

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

Price per week £295 - £398

2 bedroom, dog friendly apartment near the beach near St Helens, Isle of Wight.


This two bedroom apartment in Bembridge is small but perfectly formed. Lovingly restored by the owners, 53a offers a perfect base for a family with a light and airy double bedroom ...

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

Price per week £295 - £450

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

2 bedroom self catering apartment with sea views in Seaview, Isle of Wight.


The Crow's Nest is a second floor apartment of a Victoria property in the historic village of Seaview. Simply furnished but with wonderful views over the village rooftops to the So...

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

Price per week £295 - £375

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


35 Cross Street is a cute end of terrace townhouse with accommodation spread over three floors, and has a sunny, enclosed courtyard. Built at the turn of the century, and decorated...

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

Price per week £303 - £436

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


Faithfull Cottage is a lovingly restored, pretty mid-terrace cottage which enjoys a rear garden and countryside views on the outskirts of St Helens. This comfortable cottage is set...

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

Price per week £309 - £414

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


The perfect bolt-hole for families, 61 Drake Cottage is a comfortably furnished beach bungalow located in a small waterside development on the edge of Seaview. Just yards from the ...

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

Price per week £309 - £444

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

Price per week £312 - £437

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


With an interesting history and dating from 1852, Trevessa was once a fishing cottage and overlooks the sea. The sitting-room, dining-room and both bedrooms have beautiful sea view...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £314 - £612

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  • 10% off

    4 May 2018 - 7 May 2018

    £356.30 £320.67

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

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