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 133 luxury cottages for 5 people on the Isle of Wight

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £317

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


A deceptively spacious semi-detached Victorian property, Red House has a lovely large kitchen with both a breakfast-bar and a separate dining-area from which the enclosed garden ca...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £317

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £341

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


A Victorian property set on a quiet road and yards from the beach. Oaks is a well-equipped property, decorated to a high standard and perfect for families with open plan seating an...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £341

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

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

7 nights from £344

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


1 The Saltings is a three-bedroom, lower ground floor apartment boasting a lovely beachfront location. It would ideally suit a family with children keen to enjoy the delights of th...

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

7 nights from £344

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

7 nights from £359

2 bedroom self catering cottage at Island Harbour, near Newport.


Spring Tide is a delightful holiday cottage situated in a small development at Island Harbour Marina on the banks of the River Medina. The marina is set in a beautiful secluded val...

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

7 nights from £359

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

7 nights from £364

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


4A Ship House, an attractive townhouse positioned right in the middle of Seaview, is perfect for a family looking for a coastal break. 'Ship shape' in presentation, the fantastic t...

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

7 nights from £364

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

7 nights from £404

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


Elm Cottage is a stylish first floor apartment brimming with character and comfort. It would suit friends traveling together, a couple or a family. From the front courtyard to t...

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

7 nights from £404

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

7 nights from £413

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


This charming first floor apartment is laid over two floors and situated right in the heart of Seaview village, tucked away down a quiet side street called Rope Walk, so called as ...

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

7 nights from £413

  • Sleeps 5 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £416

2 bedroom, dog friendly holiday apartment near the beach in Shanklin.


Park Lodge Annexe is a beautifully presented lower ground floor apartment within walking distance to the Rylstone Gardens and the Chine. The cliff path is a minute stroll away, lea...

  • Sleeps 5 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £416

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

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

7 nights from £421

3 bedroom self catering cottage near the beach in Brook.


September Cottage is an excellent, family-friendly holiday home with an expansive, attractive kitchen and good-sized kitchen, sitting and dining areas. It's easy to imagine curling...

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

7 nights from £421

  • 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

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