Holiday Cottages for October

Booking a holiday cottage in October may sound like a winter break, but summer often extends its stay and graces October with glorious sunshine and warm weather. With quiet weeks and an opportunity to take the kids away for half term, there are lots of things to look forward to however you'd like to spend your holiday. Get started and browse our 1016 available cottages.Read more

We’re not promising, but it's not uncommon to be able to sit on the beach in October enjoying bright sunshine, particularly hot in a sheltered corner. And at this time of year you can also bring the dog with you as the doggy beach ban is lifted in September. Bring your bag, ball and a bowl for water, and you could spend hours playing games and relaxing on the beach, occasionally dipping your toes in the sea to cool off. October is also a great time to explore gardens and woodlands as they put on golden autumnal coats for their end of year display. Bring the family during October half-term to relive memories of a spent summer or indulge in a luxury short break before the winter kicks in. We have 1016 holiday cottages for October for you to choose from.

We've got 1016 holiday cottages available for October

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 new Owner has completely rede...

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

Price per week £320 - £459

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 £340 - £422

Our property managers are local experts who handpick perfect places to stay.

2 bedroom, dog-friendly holiday cottage with sea views in East Cowes, Isle of Wight


Smugglers' Run is a waterside property overlooking the River Medina and across to the sailing town of Cowes. Watch the boats sail by from the privacy of the balcony off the living-...

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

Price per week £344 - £450

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

Price per week £351 - £489

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


4 Tollgate Cottages features an open plan living-room with wood-burning stove for cosy nights in and a door opening out to a decked area for the warmer nights. There is outdoor sea...

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

Price per week £351 - £487

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


6 St Joseph’s has stunning panoramic sea views, which you can sit and admire from the balcony, living room and master bedroom! Ideally positioned between Bonchurch and Ventnor this...

  • Sleeps 4 + 2 cots
  • Regret no pets
  • Changeover Fri

Price per week £352 - £536

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


Yardley is a charming Victorian cottage, set in the centre of the pretty sailing village of Seaview, and just a short walk from the beach and shops. Delightfully renovated, this co...

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

Price per week £354 - £498

2 bedroom self catering apartment with sea views in Seaview.


2 Bermuda is a lovely, neutrally decorated first floor apartment with wonderful views across the Solent, a balcony for al fresco drinks and a pretty garden. With both the beach and...

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

Price per week £355 - £450

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

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


Nestled in the stunning countryside on the south west coast of the Island with far reaching sea views over the Military Road, this gorgeously converted barn is the perfect holiday ...

  • Sleeps 4 + 2 cots
  • Regret no pets
  • Changeover Fri

Price per week £357 - £607

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


One of two beautifully converted barns right in the heart of the Island's Area of Outstanding Natural Beauty. Equipped and decorated to a high standard mixing the charming features...

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

Price per week £357 - £607

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