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 164 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 164 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 164 self catering cottages for 4 on the Isle of Wight

  • Sleeps 12 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £1033

5 bedroom self catering home near the beach in Seaview, Isle of Wight.


A beautiful Edwardian villa, with evident period charm, West Ingle boasts sea views from almost every room. Spacious, light and airy, many original features have been retained. Bot...

  • Sleeps 12 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £1033

  • Sleeps 12 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1170

6 bedroom, rural self catering home with sea views in Seaview, Isle of Wight.


Bay House is an incredibly spacious and stylish Edwardian villa offering great sea views from many of its rooms. Lovingly refurbished throughout, the property is the ideal choice f...

  • Sleeps 12 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1170

  • Sleeps 12 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1440

6 bedroom, dog friendly self catering home near the beach in Ryde, Isle of Wight.


Full of character, Pelham Lodge is a top destination for a large group of friends or an extended family looking for a house for a celebratory occasion. Just a short stroll from Ryd...

  • Sleeps 12 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1440

  • Sleeps 12 + 3 cots in 3 properties
  • Changeover Fri

7 nights from £1116


Mattingley Farm is made up of three beautiful cottages, each sleeping up to four guests, and is the perfect getaway for a family or friends holiday. Dairy Cottage (3912) and Orchar...

  • Sleeps 12 + 3 cots in 3 properties
  • Changeover Fri

7 nights from £1116

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