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 151 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

151 Self Catering Cottages on the Isle of Wight

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


This contemporary studio apartment enjoys a great location in Shanklin. With modern decor and open plan living, it makes a cosy retreat for a couple looking for a coastal break. Wi...

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

Price per week £240 - £310

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


Located on the first floor of Shanklin Villa, a lovely Victorian property, this small studio apartment packs a punch despite its size. Enjoying beautiful sea views from its elevate...

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

Price per week £240 - £310

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


West Flatlet is situated right in the heart of Seaview village and is perfect for couples looking for a coastal break. This small but cosy and comfortable first floor flat sits at ...

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

Price per week £252 - £315

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 the ev...

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

Price per week £266 - £334

  • 50% off

    22 Dec 2017 - 29 Dec 2017

    £383.00 £191.50

1 bedroom self catering apartment near Ventnor, Isle of Wight


Sea Song is an attractive one bedroom, first floor apartment in the heart of beautiful communal gardens and woodlands. Perfect for romantic getaways as it is set in a rural locatio...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

Price per week £280 - £354

1 bedroom, dog friendly holiday apartment near the beach in Shanklin, Isle of Wight.


The Ivy is a compact double bedroom annexe offering comfortable accommodation for a couple seeking a relaxing island escape. Ideally located, with Shanklin village and beach a shor...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Sat

Price per week £295 - £397

1 bedroom, dog friendly cottage near the beach near Old Freshwater, Isle of Wight.


If a quintessentially English cottage is what you're after for your holiday, look no further than Afton Lodge. Set in Old Freshwater, the lodge boasts a thatched roof, stable door ...

  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £335 - £455

1 bedroom, rural self catering cottage near Newport, Isle of Wight


Little Tremore Cottage is a charming annexe situated in the historic village of Shorwell, surrounded by peaceful and idyllic countryside; this is the place to be for a romantic, re...

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

Price per week £338 - £414

2 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, well equipped throughout and extremely comfortable living room. Ma...

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

Price per week £341 - £418

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

Price per week £360 - £470

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