Cottages on the Isle of Wight Sleeping 5 People

Open the door to a Classic cottage on the Isle of Wight and feel yourself relax. All of our cottages are perfectly kitted out, combining home comforts and modern luxuries so that you can enjoy total comfort during your stay. Choose four of your favourite people or simply indulge in some extra space, our self-catering holiday cottages for 5 people are primed and ready for you on the Isle of Wight. Read more

Spring, summer, autumn and winter, a holiday on the Isle of Wight always delivers. Choose your favourite cottage from our selection and let the good times roll. Whether you are looking for a solo retreat for some gentle contemplation and relaxation, a family holiday or a catch up with friends, we'll find something for you amongst our collection of luxury cottages for 5 people. From spontaneous short breaks to holidays planned in advance with lots of time for excitement to build, give yourself something to look forward to. 

From country to coast the Isle of Wight offers a diverse and beautiful escape. Spend your days exactly the way you want to and enjoy the holiday of a lifetime. It's good news for your four-legged friend too as many of our holiday cottages are dog-friendly. 

Holiday Cottages for 5 People on the Isle of Wight 

At Classic Cottages we pride ourselves on the quality of our cottages and make sure only the best are on our books. To maintain our standards, we personally inspect and handpick all of our cottages. Each one is fully equipped with a full inventory, and everything you could need for your holiday is provided. So your experience is as relaxed and easy as can be, we provide help and support every step of the way. Get in touch to find out more. 

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

Choose from 132 luxury cottages for 5 people on the Isle of Wight

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 - £1469

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 - £1525

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

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 - £1683

4 bedroom self catering cottage with sea views near Ventnor, Isle of Wight


This large detached house is situated in an elevated position as you enter the town of Ventnor with the most breathtaking views from virtually every room. The beautiful tiered gard...

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

Price per week £715 - £1836

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


Set within a converted Victorian villa, Eversley Apartment is a large, contemporary split level apartment. With modern furnishings, this property offers a luxury option for a coast...

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

Price per week £720 - £1850

4 bedroom, rural self catering cottage near the beach near Ventnor, Isle of Wight


Located in the village of Chale, in an area of outstanding natural beauty, The Mission is a truly unique property well worth a visit. The current owners have lovingly restored this...

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

Price per week £725 - £1550

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


Hillside is a traditionally furnished Victorian holiday home located conveniently close to the pretty beaches at Seagrove and Priory Bay. Spread over four floors, there is enough s...

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

Price per week £729 - £1530

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


House of Logs is a unique and stunning property located on the west coast of the Island, just a short walk from Widdick Chine and Totland Bay. Perfect for a peaceful holiday, the h...

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

Price per week £750 - £1600

Need more time? Reserve any cottage for up to 24 hours before booking.

4 bedroom self catering cottage in Godshill, Isle of Wight


Nestled in the heart of the chocolate-box village of Godshill, this detached house has beautiful secluded gardens to the rear and everything the village can offer within a few minu...

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £765 - £1675

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


Spread over three floors The Swallows really is a beautiful family holiday home. The ground floor is very fresh, light and modern and has bi-folding doors leading out onto the pati...

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

Price per week £765 - £1796

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