Summer Holiday Cottages on the Isle of Wight

Summer Holiday Cottages on the Isle of Wight

A summer on the Isle of Wight in a Classic cottage is pretty hard to beat when it comes to finding your British summer holiday away. So why not explore all that the Isle of Wight has to offer, and in the evening return to your own private paradise. For an unforgettable summer, we have 96 holiday homes available for you to rent.  Read more

Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.

96 self-catering cottages for the summer holidays on the Isle of Wight

Sun Lodge is a 4 bedroom, dog friendly holiday cottage with sea views in Ventnor.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1449

Sun Lodge

5853

4 bedroom, dog friendly holiday cottage with sea views in Ventnor.


Step back in time and immerse yourself in the historic charm of Ventnor at this elegant Isle of Wight retreat with mesmerising sea views and generous spaces for a truly relaxing fa...

  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1449

48 Solent View is a 3 bedroom self catering cottage with sea views in Seaview.
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £821 *

48 Solent View

5828

3 bedroom self catering cottage with sea views in Seaview.


Just a short wander from the golden sands of Seagrove Bay and the quaint charm of Seaview village, this stylish holiday haven offers modern home comforts in an unbeatable location ...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £821 *

The Studio is a 1 bedroom, dog friendly, cosy cottage near Ryde.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £494

The Studio

5753

1 bedroom, dog friendly, cosy cottage near Ryde.


Whether you seek relaxation or adventure on the Isle of Wight, The Studio provides the most welcoming modern-rustic retreat to experience the best of natural beauty and contemporar...

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

7 nights from £494

The Old Dairy

  • Sleeps 7 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £1404

Bentinck is a 3 bedroom cottage near the beach in Ventnor.
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £938

Bentinck

5724

3 bedroom cottage near the beach in Ventnor.


With everything you could wish for on your doorstep for a blissful Isle of Wight holiday experience with family or friends, Bentinck is a great base to explore all that this Island...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £938

The Dairy is a 3 bedroom self catering cottage near the beach in Seaview.
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1263

The Dairy

5631

3 bedroom self catering cottage near the beach in Seaview.


Set in the pretty village of Seaview, moments from the seafront, this delightful home-from-home is waiting to welcome you. The village centre is a short stroll away, here you will ...

  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1263

Tangle Cottage is a 4 bedroom self catering cottage near the beach in Seaview.
  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1051 *

Tangle Cottage

5669

4 bedroom self catering cottage near the beach in Seaview.


Nestled at the end of Ryde Road, just a short walk from the beach and Seaview village, with off-street parking and a lovely large garden to the rear, semi-detached Tangle Cottage i...

  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1051 *

Inglefield is a 4 bedroom, dog friendly holiday cottage near the beach in St Helens.
  • Sleeps 7 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1191

Inglefield

5637

4 bedroom, dog friendly holiday cottage near the beach in St Helens.


This beautiful home close to Bembridge Harbour is a space to enjoy with family and friends. From exploring the bays and beaches to the rolling countryside and historic castles, Ing...

  • Sleeps 7 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1191

We are Gold accredited with the Green Tourism Business Scheme.

The Little Dairy Park Farm is a 2 bedroom, dog friendly holiday cottage near Ryde, Isle of Wight.
  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £910

The Little Dairy Park Farm

5636

2 bedroom, dog friendly holiday cottage near Ryde, Isle of Wight.


This welcoming retreat is close to the pretty village of Seaview and the sandy beach at Ryde, and has the Isle of Wight Gin Distillery within walking distance. Thoughtfully present...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £910

Escape Away is a 2 bedroom self catering cottage near the beach in Freshwater.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £876 *

Escape Away

5612

2 bedroom self catering cottage near the beach in Freshwater.


Close to the beach, a short drive from pretty Yarmouth and not far from the iconic Needles, Escape Away is the perfect luxury retreat to base yourself for a peaceful and relaxing h...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £876 *

Load more

Escape for a week or two by hopping on a ferry and heading to the island. It instantly feels like you're 'getting away from it all' when you travel by boat! Explore the incredible coastline, dip in the sea for a swim or two and explore all corners the Isle of Wight has to offer for a perfect self catering holiday this summer. 

Whatever you are looking for in a summer break, choose the flexibility a holiday cottage on the Isle of Wight will give you.