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 89 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

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

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £257

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


West Flatlet is situated right in the heart of Seaview village and is perfect for couples looking for a coastal break. This small but cosy and comfortable first floor flat sits at ...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £257

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  • 20% off

    31 Aug 2019 - 7 Sep 2019

    £321.75 £257.40

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £425

1 bedroom, rural self catering cottage in Newport, Isle of Wight


This absolutely gorgeous barn conversion is the perfect place for a couple's holiday, located on the Durton Farm Estate in the centre of the Island. Lovingly refurbished by the own...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £425

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

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £752

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


Sitting within a beautifully converted Victorian villa, The Cadogan Apartment offers a high standard of accommodation for a couple or lone traveller looking for a coastal break. Gu...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £752

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  • 20% off

    30 Aug 2019 - 6 Sep 2019

    £940.00 £752.00

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £362

2 bedroom self catering cottage near the beach in Seaview.


Located in a small waterside development on the edge of Seaview, 62 Buddleia Cottage is a pretty beach bungalow offering comfortable accommodation, for a couple or small family, in...

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £362

View
  • 20% off

    31 Aug 2019 - 7 Sep 2019

    £452.88 £362.30

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

7 nights from £306

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


The Crows Nest is a second floor apartment at the top of a Victorian property in the historic village of Seaview. A family looking for a convenient base from which to enjoy the Isl...

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

7 nights from £306

View
  • 20% off

    30 Aug 2019 - 6 Sep 2019

    £382.59 £306.07

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

7 nights from £389

2 bedroom, dog friendly holiday cottage near the beach in Seaview.


4 Tollgate Cottage is located near Seaview on the Duver - a beach front area that is home to the stunning Hersey Nature Reserve. This cosy cottage would suit a small family or a co...

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

7 nights from £389

View
  • 20% off

    31 Aug 2019 - 7 Sep 2019

    £486.62 £389.29

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £397

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


23 Tollgate Cottages is a comfortably furnished beach bungalow located in a small, gated waterside development on the edge of Seaview, within walking distance to the shops and cafe...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £397

View
  • 20% off

    30 Aug 2019 - 6 Sep 2019

    £496.69 £397.35

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

7 nights from £406

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


Take a few steps up to the entrance and you will find yourself in 3 Kings House, a ground floor apartment in a small development. It is the perfect base for a couple or a family wi...

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

7 nights from £406

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

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

7 nights from £422

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 set...

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

7 nights from £422

View
  • 20% off

    24 Aug 2019 - 31 Aug 2019

    £674.00 £539.20

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

7 nights from £442

2 bedroom, rural self catering apartment near the beach in Ryde.


6 Sandlands is a modest top floor apartment with a large, open plan living area, just a stroll away from Ryde's wonderfully sandy beaches, the canoe lake and the children's sand pa...

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

7 nights from £442

View
  • 10% off

    24 Aug 2019 - 31 Aug 2019

    £674.00 £606.60

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