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 178 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

178 Self Catering Cottages on the Isle of Wight

3 bedroom self catering cottage near the beach in Brook.


September Cottage is an excellent, family-friendly holiday home with an expansive, attractive kitchen and good-sized kitchen, sitting and dining areas. It's easy to imagine curling...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

Price per week £413 - £601

3 bedroom, rural self catering apartment near the beach near Newport, Isle of Wight


This stunning barn conversion is located just outside the picturesque village of Chillerton, in the heart of the Island’s farming community between Newport and Chale. The outlook o...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

Price per week £495 - £695

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


An incredibly stylish three bedroom ground floor apartment ideally located a few minutes' walk from the village of Seaview and the beach. A lovely large entrance hall centrally fra...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

Price per week £550 - £775

3 bedroom self catering cottage with sea views in Seaview, Isle of Wight.


The Old Boat House is an attractive period cottage set in a fantastic waterfront location on the edge of the beach at Seagrove Bay. This is a charming family home and can be rented...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

Price per week £567 - £861

3 bedroom, dog friendly self catering cottage in Ventnor.


This gorgeous stone cottage is nestled in a wonderful countryside location in the central south of the Island, a short distance from the coastal town of Ventnor. Situated at the en...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

Price per week £575 - £795

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


Dating back to 1863 and converted in 2011, this superb two-storey apartment is located on the outskirts of Shanklin. 10 Shanklin Manor has an elegant, monochrome interior and the u...

  • Sleeps 5
  • Regret no pets
  • Changeover Sat

Price per week £612 - £893

Don’t miss out; reserve your favourite 2019 holiday cottage for just £30

3 bedroom self catering cottage in Newport, Isle of Wight


Located in the centre of the Island on the outskirts of the town of Newport, this is perfectly located to explore different places on the Isle of Wight. In the colder months, wrap ...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

Price per week £760 - £860

3 Astra House is a comfortable first floor apartment within a converted Victorian House


3 Astra House is a comfortable first floor apartment within a converted, red brick Victorian house, located on a quiet residential no-through road in Seaview. Offering light and sp...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

Price per week £334 - £525

3 bedroom self catering cottage near the beach in St Helens, Isle of Wight.


1 Yarborough Cottage is a wonderfully quaint end of terrace property facing St Helens Green on the east side of the island, with far reaching views over Culver Downs. The owners ha...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

Price per week £358 - £563

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


24 Tollgate Cottages is a comfortable property just a stone's throw away from the beach, and a short walk from the local shops and dining in Seaview village. Situated on a small de...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £375 - £530

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