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 143 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 143 available holiday cottages and find the perfect one waiting for you. 

We have 143 self catering cottages for 4 on the Isle of Wight

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

7 nights from £362

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 £362

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

7 nights from £362

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 £362

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

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £370

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
  • Regret no pets
  • Changeover Fri

7 nights from £370

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £403

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 £403

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £403

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 £403

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £405

Quiet Corner Cottage

3646

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


Quiet Corner is a modestly furnished, comfortable, semi-detached bungalow situated in the popular village of Bembridge, less than a mile from Bembridge beach. As its name suggests ...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £405

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

7 nights from £408

Faithfull Cottage

3600

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


Faithfull Cottage is a lovingly restored, pretty mid-terrace cottage which enjoys a rear garden and countryside views on the outskirts of St Helens. This comfortable cottage is...

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

7 nights from £408

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

7 nights from £428

5 Sandpipers

3557

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


Seaview is a gorgeous, much sought-after village on the eastern edge of the Isle of Wight and 5 Sandpipers is a beautifully furnished home, perfectly positioned on a quiet street j...

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

7 nights from £428

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

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

7 nights from £428

6 Pier View Court

3559

2 bedroom self catering apartment near the beach in Ryde, Isle of Wight.


6 Pier View Court, perfectly located right on the seafront at Ryde, is a modern, well presented second floor apartment, tastefully decorated and furnished to a high standard. Relax...

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

7 nights from £428

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

7 nights from £439

Pebbles

4398

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


This beautifully refurbished house is perfectly situated in the heart of Seaview Village, with a lovely patio area to the rear and outdoor seating so you can enjoy dining in the Is...

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

7 nights from £439

Loading more