Cottages on the Isle of Wight Sleeping 5 People

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. 

Choose from 82 luxury cottages for 5 people on the Isle of Wight

7 Sandpipers is a 3 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £603

7 Sandpipers

3568

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


Perfectly situated in the heart of the popular sailing village of Seaview on the eastern side of the Isle of Wight, 7 Sandpipers is a well-equipped town house set across three floo...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £603

Sunnyside is a 3 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £767

Sunnyside

4960

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


Perfectly situated in the much sought-after village of Seaview on the Isle of Wight, Sunnyside is an appealing dog friendly holiday abode fully refurbished in 2021/22. It is set in...

  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £767

Limpets  is a 3 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
  • Sleeps 5 + cot
  • No pets
  • Changeover Sat

7 nights from £796

Limpets

4622

3 bedroom self catering apartment with sea views in Seaview, Isle of Wight.


This gorgeous home, just a stone's throw from the seafront, has sea views from the sitting-room and the luxury of your very own private garden, giving it all the ingredients for a ...

  • Sleeps 5 + cot
  • No pets
  • Changeover Sat

7 nights from £796

Sanderling is a 3 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £814

Sanderling

5424

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


A warm island welcome awaits at "Sanderling" a beautiful three bedroom home within a few minutes' walk of the beach and Seaview village, with the added bonus of a mature garden wit...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £814

10 Shanklin Manor is a 3 bedroom, rural self catering apartment near the beach in Shanklin, Isle of Wight.
  • Sleeps 5
  • No pets
  • Changeover Sat

7 nights from £834

10 Shanklin Manor

3511

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 first floor apartment is located on the outskirts of Shanklin. 10 Shanklin Manor has an elegant, monochrome interi...

  • Sleeps 5
  • No pets
  • Changeover Sat

7 nights from £834

Stargazers' Retreat is a Luxury Yurt for 5 near the beach near Ventnor, Isle of Wight.
  • Sleeps 5 + cot
  • No pets
  • Changeover Fri

7 nights from £1200

Stargazers' Retreat

5125

Luxury Yurt for 5 near the beach near Ventnor, Isle of Wight.


Welcome to Stargazers' Retreat, a heavenly glamping yurt nestled in rural splendour on the southerly tip of the Isle of Wight with blissful views of Reeth Bay and beyond. Situated ...

  • Sleeps 5 + cot
  • No pets
  • Changeover Fri

7 nights from £1200

East Gull Sands is a 3 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £512

East Gull Sands

3595

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


Seaview is a much sought-after and very charming village on the Isle of Wight and East Gull Sands sits in a magical position overlooking the beach, just a short stroll away from th...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £512

Lanthorn Cottage is a 3 bedroom, dog friendly holiday cottage near the beach in St Helens, Isle of Wight
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £551

Lanthorn Cottage

4287

3 bedroom, dog friendly holiday cottage near the beach in St Helens, Isle of Wight


Located in a quiet side street just off the village green in St Helens, this cosy cottage offers great accommodation with a good sized garden, spacious decking and outdoor seating ...

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

7 nights from £551

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

Pandora Lodge is a 3 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £597

Pandora Lodge

3642

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


Perfectly situated in the heart of the delightful village of Seaview on the Isle of Wight, Pandora Lodge is a lovely, spacious ground floor apartment forming part of a larger prope...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £597

25 Palmerston Road is a 3 bedroom self catering cottage near the beach in Shanklin.
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £599

25 Palmerston Road

3538

3 bedroom self catering cottage near the beach in Shanklin.


Welcome to 25 Palmerston Road, a delightful holiday home perfectly situated in the charming town of Shanklin and just a short stroll away from the golden sandy beach and a good sel...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £599

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