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 181 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

181 Self Catering Cottages on the Isle of Wight

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


Beautifully decorated in neutral tones throughout, Alcantara is a well-presented, spacious property offering flexible family accommodation. This detached property has a ground floo...

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

Price per week £500 - £676

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


A smart town house, with well presented accommodation for eight set over three floors, Lucaya offers a great space with a pretty enclosed rear patio and lawn for an extended family...

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

Price per week £532 - £777

3 bedroom, dog friendly holiday cottage with sea views in Brook, Isle of Wight


This pretty detached cottage can be found on a quiet lane in Brook on the south west coast. With its large, mature garden overlooking adjacent farmland, and close proximity to mile...

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

Price per week £534 - £857

4 bedroom self catering apartment near the beach in Seaview.


Crowsteps is on the first and second floor of a property tucked away in Seaview in a semi detached property. Boasting a stunning roof terrace with far reaching views over the Solen...

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

Price per week £563 - £829

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


This bright, spacious detached house, on a quiet lane is just a 10 minute walk from the beautiful beach at Seagrove Bay. Furnished to a high standard, with four good-sized bedrooms...

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

Price per week £599 - £869

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


A spacious family home, 17 Sandcove Rise is located in a quiet cul-de-sac in the pretty village of Seaview. Well-presented and with modern furnishings throughout, it has a wonderfu...

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

Price per week £630 - £909

Dogs go free on holidays starting between 29th June to 5th July.

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


Middle Salterns is a pretty, end of terrace Edwardian property in the heart of Seaview, simply decorated and arranged over three floors. There are two double bedrooms and a bunk-ro...

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

Price per week £643 - £827

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


Mallards is a spacious, three-storey Edwardian house in Seaview village and a much-loved family home. Enjoying a great location just yards from the seafront, it's the perfect choic...

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

Price per week £664 - £867

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


Bay View is a charming semi-detached house situated down a quiet leafy lane off the Green in the picturesque village of St Helens and aptly named due to the stunning views over St ...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Sat

Price per week £675 - £910

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


The owners of 24 Sandcove Rise didn’t buy a television for the first few years of owning this property, as the sea views from the sitting-room made better viewing! Don’t panic, the...

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

Price per week £710 - £1000

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