Luxury Cottages for 4 People on the Isle of Wight

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 125 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 125 available holiday cottages and find the perfect one waiting for you. 

We have 125 self catering cottages for 4 on the Isle of Wight

The Beach Retreat is a 2 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 4
  • No pets
  • Changeover Fri

7 nights from £390

The Beach Retreat

3665

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


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
  • No pets
  • Changeover Fri

7 nights from £390

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  • 10% off

    26 Apr 2024 - 3 May 2024

    £552.00£496.80

Hove To is a 2 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £403

Hove To

3767

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


Hove To is one of a 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 over th...

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

7 nights from £403

Cockleshells is a 2 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £403

Cockleshells

3815

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 accommodation offers a double...

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

7 nights from £403

Sugar Beach is a 2 bedroom self catering cottage near the beach in Seaview, Isle of Wight
  • Sleeps 4
  • No pets
  • Changeover Sat

7 nights from £407

Sugar Beach

5102

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


Seaview is a much sought-after charming village on the east of the Isle of Wight, and Sugar Beach is perfectly situated just a stone's throw from the beach and a short stroll away ...

  • Sleeps 4
  • No pets
  • Changeover Sat

7 nights from £407

Berry Cabin is a 2 bedroom, dog friendly, self catering cottage in Seaview, Isle of Wight.
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £428

Berry Cabin

5286

2 bedroom, dog friendly, self catering cottage in Seaview, Isle of Wight.


What a little cutie! Berry Cabin is a delightful bolthole for four guests and one well behaved doggy looking for some summer fun! Surrounded by Hersey nature reserve and countrysid...

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

7 nights from £428

Dairy Cottage is a 2 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £449

Dairy Cottage

3912

2 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight


Originally the farm's milking parlour, Dairy Cottage is a light and airy single-storey cottage with plenty of charm throughout. Mattingly Farm is made up of three barns in total Da...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £449

Orchard Cottage is a 2 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £449

Orchard Cottage

3936

2 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight


Originally the farm's milking parlour, this delightful semi-detached cottage sleeping four is the perfect cottage to spend quality time together as a family in a stunning rural loc...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £449

Oakham Cottage is a 2 bedroom, dog friendly holiday cottage in a rural setting close to Godshill, Isle of Wight
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £468

Oakham Cottage

3516

2 bedroom, dog friendly holiday cottage in a rural setting close to Godshill, Isle of Wight


Oakham Cottage can be found in the heart of the Isle of Wight, surrounded by rolling countryside and the perfect location for exploring all treasures this lovely Island has to offe...

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

7 nights from £468

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

2 Bermuda is a 2 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £468

2 Bermuda

3517

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


Welcome to 2 Bermuda, a rather lovely first floor apartment nestled in the charming village of Seaview, with wonderful views stretching across the Solent - ideal for an unforgettab...

  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £468

Grafton Cottage is a 2 bedroom, dog friendly cottage in a rural setting close to Godshill, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £468

Grafton Cottage

3501

2 bedroom, dog friendly cottage in a rural setting close to Godshill, Isle of Wight.


Located in a tranquil rural setting and part of Bagwich House, this sympathetic barn conversion is set over two floors and is one of three holiday properties. A short drive from th...

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

7 nights from £468

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