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. 

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 131 luxury cottages for 5 people on the Isle of Wight

4 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight


With stunning sea views from not one but two balconies Solent View Road is a wonderful holiday destination within a few minutes' walk from Seagrove Bay. Located just on the outskir...

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

Price per week £825 - £1887

View
  • 20% off

    19 Oct 2018 - 26 Oct 2018

    £1199.91 £959.93

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


Walnut Cottage is a real find if you're looking for a spot of luxury on holiday. Tucked away in central Seaview village Walnut offers spacious accommodation over two floors and an ...

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

Price per week £835 - £2095

View
  • 20% off

    19 Oct 2018 - 26 Oct 2018

    £1494.99 £1195.99

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


Tides Reach is a wonderful, newly modernised family house along the Seaview Duver just a short walk into Seaview Village and the Yacht Club. Tides Reach has a stylish open plan sit...

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

Price per week £850 - £1683

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


A wonderful contemporary beach house, offering accommodation for eight, within a few minute's walk to the beach and Bembridge village. There is a spacious kitchen/diner with doors ...

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

Price per week £850 - £1900

Choose from our exclusive collection at the best prices with real time availability.

4 bedroom converted barn with far reaching rural views in St Helens, Isle of Wight.


Hill Farm Barn is an immaculately presented and impressively converted 18th Century Threshing Barn standing in half acre of private grounds. Perched on a hilltop half a mile from a...

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

Price per week £995 - £2370

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


This pretty attached Victorian cottage sits in the grounds of the Priory Estate and comes with use of its many diversions. With 70 acres of grounds to explore, plus a stunning priv...

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

Price per week £1013 - £2610

View
  • 20% off

    19 Oct 2018 - 26 Oct 2018

    £1530.24 £1224.19

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


A spectacular waterfront three-storey house situated on Seaview duver with uninterrupted sea views from the kitchen/dining-room and the first floor balcony. Just a few steps from y...

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

Price per week £1100 - £2700

4 bedroom, rural self catering cottage with estuary views near Newport, Isle of Wight


This superb property overlooks the River Medina from its corner plot in the exclusive Island Harbour development. Laid over four storeys offering stunning views across the River Me...

  • Sleeps 8
  • Regret no pets
  • Changeover Sat

Price per week £1200 - £2800

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


This beautiful house is set in several acres of garden on the outskirts of Yarmouth, just a few minutes walk to the water’s edge, a truly stunning holiday destination. The property...

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

Price per week £1375 - £2800

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


6 Seafield Terrace is a charming terraced cottage set in the pretty village of Seaview. With spacious accommodation spread over three floors, and the beach close at hand, it makes ...

  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £647 - £1469

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

Loading more