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 119 luxury cottages for 5 people on the Isle of Wight

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

7 nights from £438

3 bedroom self catering cottage near the beach in Seaview.


This modern, well-presented townhouse situated in a small development in the centre of Seaview would suit a family, a couple or several friends traveling together. It really is...

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

7 nights from £438

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  • 10% off

    5 Apr 2019 - 12 Apr 2019

    £626.00 £563.40

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

7 nights from £444

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


Nestled in the heart of Seaview village, this lovely ground floor apartment is a stone's throw from both the coastline and village amenities, in fact it is just steps away from a f...

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

7 nights from £444

View
  • 10% off

    29 Mar 2019 - 5 Apr 2019

    £510.00 £459.00

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

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £445

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


Set in the delightful sailing village of Seaview, Blackberries is a pretty, refurbished cottage which offers a peaceful escape for families, small groups or couples alike. Comforta...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £445

View
  • 10% off

    30 Mar 2019 - 6 Apr 2019

    £502.81 £452.53

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

7 nights from £462

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


A hidden gem tucked away on Bluett Avenue in the peaceful Victorian village of Seaview, Lawn End makes great use of accent colours in its interior decor presenting a beautiful holi...

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

7 nights from £462

View
  • 10% off

    29 Mar 2019 - 5 Apr 2019

    £530.61 £477.55

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £470

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


The wow factor at 4 Commodores Court is the location; perched directly opposite the beach, it offers stunning views of The Solent to the front, and delightful rural and lakeside vi...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £470

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £479

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


Formerly the officer's quarters of the coastguard station, 6 Coastguard Cottages has been beautifully decorated and offers a wonderful holiday home in Brook. This period property h...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £479

View
  • 10% off

    11 May 2019 - 18 May 2019

    £608.95 £548.10

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

7 nights from £480

3 bedroom self catering apartment near the beach in Seaview.


With a comfortable interior, an unbeatable location, manicured grounds and the beach within easy reach, 3 Springfield Court has it all. This delightful holiday home would suit a fa...

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

7 nights from £480

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

7 nights from £480

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


Merries is a traditional beachside bungalow conveniently situated between Puckpool Park and Seaview village centre. It would suit a family wanting a convenient coastal holiday base...

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

7 nights from £480

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.

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

7 nights from £480

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


The Barn, a linked country cottage with a rustic interior and some exposed wooden beams, is located on the outskirts of Merstone and just minutes from the quaint village of Godshil...

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

7 nights from £480

View
  • 15% off

    30 Mar 2019 - 6 Apr 2019

    £565.02 £480.27

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

7 nights from £481

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


Trevenna is a thoughtfully designed holiday home in Seaview that really delivers when it comes to space, charm and comfort. It would be ideal for a family or several couples travel...

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

7 nights from £481

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