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 61 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 61 self catering cottages available to rent in June on the Isle of Wight

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

7 nights from £304

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


This charming one bedroom apartment forms part of a country house, set around a shared Spanish-style courtyard, just outside the bustling village of Bembridge. You can enjoy the ev...

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

7 nights from £304

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  • 10% off

    9 Aug 2019 - 16 Aug 2019

    £470.00 £423.00

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £400

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 £400

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

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

7 nights from £422

1 bedroom self catering cottage near Ventnor, Isle of Wight


Located in a rural village setting, Berryl Mead View is a delightful home from home cottage with plenty of space, well equipped throughout and extremely comfortable living room wit...

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

7 nights from £422

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

7 nights from £381

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 £381

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

7 nights from £402

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


Cockleshells is one of the charming Salterns bungalows situated along the Seaview Duver within a short walk to the Yacht Club and Seaview Village. The new Owner has completely rede...

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

7 nights from £402

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

7 nights from £419

2 bedroom self catering apartment with sea views in Seaview.


2 Bermuda is a lovely, neutrally decorated first floor apartment with wonderful views across the Solent, a balcony for al fresco drinks and a pretty garden. With both the beach and...

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

7 nights from £419

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

7 nights from £434

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


Newlands is a charming detached cottage located just off the Green, in the picturesque village of St Helens. Its location is very peaceful yet within walking distance to the villag...

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

7 nights from £434

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

7 nights from £443

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


5 Sandpipers is a well-equipped, modern house set within a small development in the heart of Seaview. It offers comfortable accommodation for a couple or small family. The sitt...

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

7 nights from £443

Our property managers are local experts who handpick perfect places to stay.

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £461

2 bedroom, dog friendly cottage in a rural setting close to Godshill, Isle of Wight.


A barn conversion, in a rural setting, with a welcoming, rustic feel to it, 1 Bagwich Barn offers an ideal base in the middle of the The Isle of Wight, from which to explore north ...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £461

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £461

2 bedroom, dog friendly holiday cottage in a rural setting close to Godshill, Isle of Wight


A barn conversion in a rural setting, you'll enjoy a feeling of peace from the moment you step inside this lovely retreat, with its exposed beams and rustic decor. Sitting within t...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £461

View
  • 20% off

    20 Jul 2019 - 27 Jul 2019

    £796.00 £636.80

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