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 116 luxury cottages for 5 people on the Isle of Wight

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

7 nights from £425

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


The location of 40 Trelawny Way, on a quiet residential road in Bembridge, belies its extravagant interior. For those looking for a family home with an interior decorated with arti...

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

7 nights from £425

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

7 nights from £505

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

7 nights from £505

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £550

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

7 nights from £550

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

7 nights from £561

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

7 nights from £561

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

  • Sleeps 9 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £570 *

5 bedroom, rural self catering cottage near the beach 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 charming family home has been tastefully d...

  • Sleeps 9 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £570 *

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

7 nights from £600

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


A very charming house overlooking The Green in the picturesque village of St Helens, on the east side of the Island, within a short and scenic walk to the beach. A footpath startin...

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

7 nights from £600

  • Sleeps 5
  • Regret no pets
  • Changeover Sat

7 nights from £624

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

7 nights from £624

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

7 nights from £341

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

7 nights from £341

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

7 nights from £366

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

7 nights from £366

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £383

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


10 Tollgate Cottages is a pastel coloured, beach bungalow set in a small gated development close to the waterfront. Clean, neutral decor and its close proximity to the beach make t...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £383

Our guests rate us 4.8/5 on Feefo, the independent review site.

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