Luxury Cottages for 4 People on the Isle of Wight

Enjoy a luxury island retreat and book a holiday cottage for up to four people on the Isle of Wight. There's room for you and three of your nearest and dearest, and many of our cottages are dog-friendly too. Browse through our selection of 165 available self-catering cottages and take a step closer to the holiday of a lifetime.Read more

Spending time with our friends and family is really important, but it's not always that easy to get together and catch up. Holiday cottages provide great neutral ground in beautiful settings, away from the distractions of everyday life. Spend time together in a luxury self catering cottage sleeping up to 4 people and rediscover yourselves.

Self Catering Cottages on the Isle of Wight for Four People

At Classic Cottages we pride ourselves on marketing only the finest holiday cottages on the Isle of Wight. Each one of our self catering cottages is personally inspected and fully equipped to ensure your total comfort. Take your time looking through our collection of 165 available holiday cottages and find the perfect one waiting for you. 

Isle of Wight Ferry Booking With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing

We have 165 self catering cottages for 4 on the Isle of Wight

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £290

2 bedroom self catering cottage near the beach in Seaview.


This delightful, stylish seafront bungalow is located in a front row position with wonderful views of the Solent and the beach is practically on the doorstep. Days at the seaside, ...

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £290

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £301

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


Take a few steps up to the entrance and you will find yourself in 3 Kings House, a ground floor apartment in a small development. It is the perfect base for a couple or a family wi...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £301

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

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £301

2 bedroom, dog friendly apartment near the beach in Bembridge, Isle of Wight.


This two bedroom apartment in Bembridge is small but perfectly formed. Lovingly restored by the owners, 53a offers a perfect base for a family with a light and airy double bedroom ...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £301

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £301

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


The Crows Nest is a second floor apartment at the top of a Victorian property in the historic village of Seaview. A family looking for a convenient base from which to enjoy the Isl...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £301

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £316

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


The perfect bolt-hole for families, 61 Drake Cottage is a comfortably furnished beach bungalow located in a small waterside development on the edge of Seaview. Just yards from the ...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £316

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £319

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


The Lobster Pot is a comfortably furnished beach bungalow located in a small waterside development on the edge of Seaview and next to a nature reserve. This beach bolt hole has dec...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £319

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £320

2 bedroom, rural self catering apartment near the beach in Ryde.


6 Sandlands is a modest top floor apartment with a large, open plan living area, just a stroll away from Ryde's wonderfully sandy beaches, the canoe lake and the children's sand pa...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £320

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £320

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


Hove To is one of a small collection of bungalows located along the Seaview Duver. Situated on the corner, it benefits from a large decked area on two sides with a lovely outlook o...

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £320

Our guests rate us 4.8/5 on Feefo, the independent review site.

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £320

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


Cockleshells is one of the charming Salterns bungalows situated along the Seaview Duver within a short walk to the Yacht Club and Seaview Village. The new Owner has completely rede...

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £320

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £328

2 bedroom, dog-friendly holiday cottage with sea views in East Cowes, Isle of Wight


Smugglers' Run is a waterside property overlooking the River Medina and across to the sailing town of Cowes. It would suit a family or a couple in need of a little extra space. ...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £328

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