Holiday Cottages for June on the Isle of Wight

A healthy dose of summer sunshine and fresh air can provide more than just the ingredients for a great holiday. A stay on the Isle of Wight can relax the mind and revive the soul. Make the most of the June calm ahead of the summer crowds and enjoy a blissful retreat. We have a selection of 126 luxury self catering cottages to choose from. Read more

Pack a picnic and hike across the coastal paths, or make the most of quiet beaches and soak up the sun and salty sea air. A stay on the Isle of Wight this June can provide some much needed TLC and a well-deserved break. Whoever you want to spend your time with, whether you'd prefer a solo retreat, a family break, a gathering with friends or an escape with the dog, we have a wonderful portfolio of luxury cottages ready for you to choose from. Quaint rural cottages to seaside retreats, we have a huge variety of cottages available. All you have to do? Pick your favourite one. Or two. Or three.

Isle of Wight Cottages for Rent this June

Treat yourself to a luxury break on the Isle of Wight this June. This island paradise begs to be explored, and we have a luxury collection of self catering cottages offering the perfect base. 

At Classic Cottages, we know what makes great accommodation. All of our cottages are handpicked and personally inspected, and each is fully equipped ensuring your total comfort. Many of our cottages are dog friendly too, so you don't have to leave your friend behind this June.

For more information, browse our selection and find the right cottage for you. If you have any questions, don't hesitate to get in touch

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

We have 126 self catering cottages available to rent in June on the Isle of Wight

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £795

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


This lovely, light and spacious detached house located on Fairy Road in Seaview, just a short stroll from the seafront, makes a fantastic base for a wonderful holiday on the Isle o...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £795

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

7 nights from £795

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


Right in the heart of Seaview village, this semi-detached property has been completely renovated, with a Skandi theme, to offer a wonderful place to stay on the Isle of Wight. With...

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

7 nights from £795

View
  • 10% off

    29 Mar 2019 - 5 Apr 2019

    £739.56 £665.61

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

7 nights from £850

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


Primrose Cottage is a fully modernised and beautifully furnished Victorian three bedroom cottage situated just off the green in St Helens and offering everything you might need for...

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

7 nights from £850

  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £875

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


A simply gorgeous three bedroom property just off St Helens' green on the eastern side of the Isle of Wight, The Haven is just a short walk from the coast and a ten minute stroll t...

  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £875

View
  • 10% off

    23 Mar 2019 - 30 Mar 2019

    £815.95 £734.40

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

7 nights from £559

3 bedroom, dog friendly holiday cottage near the beach in Totland, Isle of Wight


If you long for picturesque walks in the daytime and quiet nights under starry skies, then Ashmead Cottage is your holiday ideal. This lovely property would suit a family or even t...

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

7 nights from £559

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £676

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


This light, beautifully presented holiday home offers quality accommodation with wooden floors, whitewashed walls and interesting prints and furnishings lending splashes of colour ...

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £676

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

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £845

4 bedroom, rural self catering cottage on the outskirts of Wootton, Isle of Wight


This gorgeous stone cottage is tucked away in the most idyllic and tranquil location, surrounded by fields and woodland, this is the perfect holiday setting to truly escape from it...

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £845

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £850

3 bedroom self catering apartment with sea views in Seagrove Bay, Isle of Wight


In the most spectacular location just a few metres from Seagrove Bay, this two-storey apartment is in a prime holiday location with a large decked balcony to admire the stunning se...

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £850

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1395

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


Montagu is a luxurious, upper ground floor apartment forming part of a converted Victorian villa, just seconds from the beach at Shanklin. With a private patio with sea views and a...

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1395

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  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £794.81 £635.84

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £579

4 bedroom self catering cottage near the beach in Binfield, Isle of Wight.


Tradewinds is a four bedroomed yachtsman house, located within a waterside marina development of Island Harbour, just outside of Newport. There is a small courtyard to the rear of ...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £579

View
  • 20% off

    30 Mar 2019 - 6 Apr 2019

    £522.54 £418.03

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