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 198 available self-catering cottages and take a step closer to the holiday of a lifetime.

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 198 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 198 self catering cottages for 4 on the Isle of Wight

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


Right in the heart of Seaview village, this semi-detached property has been completely renovated, with a Skandi theme, to offer a wonderful place to stay on the Isle of Wight. With...

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

3 Astra House is a comfortable first floor apartment within a converted Victorian House


3 Astra House is a comfortable first floor apartment within a converted, red brick Victorian house, located on a quiet residential no-through road in Seaview. Offering light and sp...

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

Price per week £334 - £825

Don’t miss out; reserve your favourite 2019 holiday cottage for just £30

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


1 Yarborough Cottage is a wonderfully quaint end of terrace property facing St Helens Green on the east side of the island, with far reaching views over Culver Downs. The owners ha...

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

Price per week £358 - £888

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 has stunning views of the Solent from the front, and delightful rural and lakeside view...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £374 - £930

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  • 30% off

    7 Sep 2018 - 14 Sep 2018

    £534.19 £373.80

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


27 Tollgate Cottages is one of a number of well presented, beachfront holiday bungalows situated in Salterns Village, a small gated development located opposite Seaview Duver and b...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £375 - £830

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


24 Tollgate Cottages is a comfortable property just a stone's throw away from the beach, and a short walk from the local shops and dining in Seaview village. Situated on a small de...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £375 - £830

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


10 Tollgate Cottages is a pastel coloured, beach bungalow set in a small gated development close to the waterfront. Clean, neutral decor and its close proximity to the beach make t...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £375 - £830

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


6 Tollgate Cottages is a bright and cheery cottage set in a small, gated development near the pretty village of Seaview. Close to the beach, local shops and bars, and with Cafe Blu...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £375 - £830

Choose from our exclusive collection at the best prices with real time availability.

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


This modern and bright bungalow with a south-facing garden is perfect for a family holiday and as it has a fully-enclosed rear garden, why not bring your four-legged friends? Sleep...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £384 - £850

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


1 Astra House is a comfortable, light and bright ground floor apartment set within a charming Victorian property in Seaview. Featuring an open plan layout, the dining-area, kitchen...

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

Price per week £398 - £895

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