School Summer Holiday Cottages on the Isle of Wight

A summer on the Isle of Wight in a Classic cottage combines the ultimate holiday experience with luxury self-catering accommodation. Head out and about during the day and 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 107 holiday homes available for you to rent. Read more

The school holidays are finally here! Now, what to do with them? A whole six weeks of entertaining the children on top of everything else can be a struggle, so why not escape for a week or two by heading west. Leave the children with the grandparents for a romantic break away to recharge your batteries, or take advantage of some true family time and have a holiday to remember in a holiday cottage. 

Granny and Grandpa can come along and relax (and maybe keep an eye on the kids so you can have a quiet dinner out one evening?) Or bring your friends and their family for one big fun experience in either a large manor house or two separate cottages side by side. Holiday near the sea for bucket and spade beach days, or stay further in land to enjoy panoramic hilltop views and dog walking havens – the moors are a great place to holiday if you want to bring your four-legged friend.

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

Isle of Wight Ferry Booking With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing

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

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £614

3 bedroom self catering cottage near the beach in Brook.


September Cottage is an excellent, family-friendly holiday home with an expansive, attractive kitchen and good-sized kitchen, sitting and dining areas. It's easy to imagine curling...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £614

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £790

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


An incredibly stylish three bedroom ground floor apartment ideally located a few minutes' walk from the village of Seaview and the beach. A lovely large entrance hall centrally fra...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £790

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £795

3 bedroom, dog friendly self catering cottage in Ventnor.


This gorgeous stone cottage is nestled in a wonderful countryside location in the central south of the Island, a short distance from the coastal town of Ventnor. Situated at the en...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £795

View
  • 10% off

    20 Apr 2019 - 27 Apr 2019

    £575.04 £517.50

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £900

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


A very charming house overlooking The Green in the picturesque village of St Helens, on the east side of the Island, within a short and scenic walk to the beach. A footpath startin...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £900

  • Sleeps 5
  • Regret no pets
  • Changeover Sat

7 nights from £911

3 bedroom, rural self catering apartment near the beach in Shanklin, Isle of Wight.


Dating back to 1863 and converted in 2011, this superb two-storey apartment is located on the outskirts of Shanklin. 10 Shanklin Manor has an elegant, monochrome interior and the u...

  • Sleeps 5
  • Regret no pets
  • Changeover Sat

7 nights from £911

View
  • 10% off

    30 Mar 2019 - 6 Apr 2019

    £676.52 £608.87

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £541

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

7 nights from £541

View
  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £431.72 £345.37

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

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £541

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

7 nights from £541

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £541

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

7 nights from £541

View
  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £431.72 £345.37

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

7 nights from £575

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

7 nights from £575

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

7 nights from £582

3 bedroom self catering apartment near the beach in Seaview.


Pandora Lodge is a lovely ground floor apartment forming part of a larger Victorian property in central Seaview. With sea views from the sitting-room and large bay windows featured...

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

7 nights from £582

View
  • 20% off

    6 Apr 2019 - 13 Apr 2019

    £581.79 £465.43

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