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 124 luxury cottages for 5 people on the Isle of Wight

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 - £2500

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

4 bedroom, rural self catering cottage with estuary views near Newport.


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

  • Sleeps 8
  • Regret no pets
  • Changeover Fri

Price per week £1400 - £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 - £1440

Our property managers are local experts who handpick perfect places to stay.

5 bedroom self catering cottage near the beach in Ryde, Isle of Wight.


Middle Lodge is a gorgeous 1860s, stone-built, Victorian holiday home set in a mature enclosed garden on the edge of Ryde on the east of the island. The outside is charmingly perio...

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

Price per week £704 - £1622

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


2 Little Cedars is a sleek and modern property, with a light and clean finish throughout. Split over three floors, and stylishly decorated with luxury furnishings, this delightful ...

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

Price per week £794 - £2132

5 bedroom, dog friendly holiday cottage with sea views in Ventnor.


Woodlands offers a perfect retreat for friends and family to spend quality time together in a stunning Grade II listed Victorian villa in the cosmopolitan town of Ventnor. With amp...

  • Sleeps 9 + 3 cots
  • Dogs welcome
  • Changeover Fri

Price per week £813 - £2350

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 is a charming family home and can be rented...

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

Price per week £931 - £2360

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  • 15% off

    3 Aug 2018 - 10 Aug 2018

    £2360.00 £2006.00

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


Barton Manor Farmhouse is a beautifully refurbished, 150 year old property set in the delightful grounds of the Barton Estate, adjacent to English Heritage's Osborne House, former ...

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £1277 - £3120

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


Orchard House is a wonderful property for an extended family looking for a sprawling holiday home near the beach in Bembridge. The downstairs living areas are inviting - no doubt t...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £717 - £1928

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

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