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 107 holiday homes available for you to rent. Read 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. 

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

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

Newclose Houseboat is a 4 bedroom houseboat with sea views in Bembridge, Isle of Wight
  • Sleeps 8
  • No pets
  • Changeover Sat

7 nights from £1868 *

Newclose Houseboat

5200

4 bedroom houseboat with sea views in Bembridge, Isle of Wight


Welcome aboard Newclose Houseboat, a beautifully restored contemporary houseboat located in picturesque Bembridge harbour on the Isle of Wight, just a short stroll away from the st...

  • Sleeps 8
  • No pets
  • Changeover Sat

7 nights from £1868 *

10 Bayclose is a 2 bedroom self catering apartment with sea views in Freshwater, Isle of Wight
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £756

10 Bayclose

5159

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


Overlooking the gorgeous coastline at Freshwater Bay sits 10 Bayclose, a wonderfully homely apartment perfect for a family getaway to the seaside. With light and airy interiors, sn...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £756

Stargazers' Retreat is a Luxury Yurt for 5 with sea views and outdoor bathtubs near Ventnor, Isle of Wight.
  • Sleeps 5 + cot
  • No pets
  • Changeover Fri

From £237 per night *

Stargazers' Retreat

5125

Luxury Yurt for 5 with sea views and outdoor bathtubs near Ventnor, Isle of Wight.


Welcome to Stargazers' Retreat, a heavenly glamping yurt nestled in rural splendour on the southerly tip of the Isle of Wight with blissful views of Reeth Bay and beyond. Situated ...

  • Sleeps 5 + cot
  • No pets
  • Changeover Fri

From £237 per night *

Sheldonia is a 3 bedroom self catering cottage with sea views in Ventnor, Isle of Wight.
  • Sleeps 6
  • No pets
  • Changeover Sat

7 nights from £979 *

Sheldonia

5109

3 bedroom self catering cottage with sea views in Ventnor, Isle of Wight.


Welcome to Sheldonia, a hidden gem in the delightful seaside town of Ventnor and within touching distance of Steephill Cove - one of the Island's prettiest beaches, featured in The...

  • Sleeps 6
  • No pets
  • Changeover Sat

7 nights from £979 *

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

7 nights from £553

Sugar Beach

5102

2 bedroom dog friendly 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
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £553

Underwood Cabin is a 3 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1406

Underwood Cabin

4995

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


Nestled in the beautiful grounds of St Hubert's Lodge and surrounded by tranquil woodlands and green pastures, Underwood Cabin is a delightful island retreat, perfectly situated be...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1406

Choose our flexible booking option and have the ability to cancel anytime.

18 Seaview Bay is a 1 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
  • Sleeps 2
  • No pets
  • Changeover Sat

7 nights from £700

18 Seaview Bay

4996

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


Perfectly situated in the much sought-after village of Seaview on the Isle of Wight, 18 Seaview Bay is a charming, sunny apartment found in a small development, close to the villag...

  • Sleeps 2
  • No pets
  • Changeover Sat

7 nights from £700

Sea Lights is a 2 bedroom coastal holiday home, with sea views in Cowes, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1406

Sea Lights

4967

2 bedroom coastal holiday home, with sea views in Cowes, Isle of Wight.


Situated close to the beating heart of world-famous Cowes, lies the pretty coastal village of Gurnard, where you will find this handsome coastal ground floor pet-friendly apartment...

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

7 nights from £1406

Valdora is a 3 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £1254

Valdora

4959

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


Perfectly situated in the heart of the charming village of Seaview, Valdora is a gorgeous holiday retreat, beautifully styled to offer the very best in contemporary living. Seaview...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £1254

19 Seaview Bay is a 1 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 2
  • No pets
  • Changeover Sat

7 nights from £700

19 Seaview Bay

4926

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


Escape to the delights of 19 Seaview Bay to enjoy a slice of stunning Island coastline, a gentle stroll around the pretty local shops, relax with an afternoon tea at Seaview Hotel ...

  • Sleeps 2
  • No pets
  • Changeover Sat

7 nights from £700

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