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 193 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 193 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 193 self catering cottages for 4 on the Isle of Wight

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


A seaside sanctuary, Shore House is a three-storey beautifully decorated house, with its own private heated swimming pool. Making the most of the far reaching views over the Solent...

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

Price per week £580 - £1474

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


A classic red brick Victorian home, with lovely bay windows adding to the period charm, Haslemere is a family home just a short walk from Yarmouth village. The property has an invi...

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

Price per week £588 - £1010

3 bedroom self catering cottage near the beach in Seaview.


In a quiet position within a secluded courtyard in Seaview, Raleigh Cottage is complete with a cosy wood-burning stove for the cooler months, lovely decking for outside dining and ...

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

Price per week £625 - £1400

3 bedroom, dog friendly cottage near the beach in Bembridge.


Ledge View is a beautifully renovated semi-detached home just steps away from Forelands beach, lined with quirky beach huts, stretches of white sand, rock pools and an acclaimed ca...

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

Price per week £648 - £1420

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

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


A simply gorgeous three bedroom property just off St Helens' green on the eastern side of the Isle of Wight, The Haven is just a short walk from the coast and a ten minute stroll t...

  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £650 - £1500

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


A gorgeous Victorian three bedroom house on the outskirts of Shanklin with a lovely secluded garden and a private swimming pool. Beautifully decorated throughout, the Owner has tak...

  • Sleeps 6
  • Regret no pets
  • Changeover Fri

Price per week £706 - £1595

3 bedroom cottage with hot tub and sea views in Ryde, Isle of Wight


This absolutely stunning property is laid over five mezzanine floors, has two sea-facing balconies and a hot tub with a sea view! Beautifully decorated throughout, The Lodge offers...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

Price per week £795 - £1500

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


Flackstead is a unique eco-friendly house which has breath-taking and uninterrupted coastal views across Compton Bay towards the Needles. Flackstead combines the very best of conte...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £1650 - £2950

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


Ashmead Cottage has been thoughtfully decorated throughout offering three lovely bedrooms and two modern bathrooms. The kitchen opens out onto a charming private decked-area with o...

  • Sleeps 7 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £437 - £990

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


This light, beautifully presented holiday home offers quality accommodation with wooden floors, whitewashed walls and interesting prints and furnishings lending splashes of colour ...

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

Price per week £499 - £1325

Our property managers are local experts who handpick perfect places to stay.

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