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 122 luxury self catering cottages to choose from. 

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

2 bedroom, dog friendly apartment near the beach near St Helens, Isle of Wight.


This two bedroom apartment in Bembridge is small but perfectly formed. Lovingly restored by the owners, 53a offers a perfect base for a family with a light and airy double bedroom ...

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

Price per week £395 - £575

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


Number 18 is a two bedroomed chalet on the small Tollgate holiday complex on the Seaview Duver. These are ideal to rent out for larger families as you can rent next door and other ...

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

Price per week £400 - £595

View
  • 20% off

    7 Jul 2018 - 14 Jul 2018

    £594.80 £475.84

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

Price per week £400 - £595

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


Yardley is a charming Victorian cottage, set in the centre of the pretty sailing village of Seaview, and just a short walk from the beach and shops. Delightfully renovated, this co...

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

Price per week £415 - £625

Dogs go free on holidays starting between 29th June to 5th July.

2 bedroom, dog friendly holiday cottage near the beach in 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

Price per week £448 - £666

View
  • 20% off

    7 Jul 2018 - 14 Jul 2018

    £665.81 £532.65

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


Westbourne Cottage is a pretty, pastel-coloured, holiday cottage, located in the picturesque Seagrove Bay. The single level accommodation (ideal for less able guests) is lightly de...

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

Price per week £451 - £692

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


Originally the farm's milking parlour, this delightful cottage sleeping four is the perfect cottage to spend quality time together as a family in a stunning rural location. Located...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £468 - £529

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


Fir Cottage is an attractive and contemporary conversion of a Victorian home, located right in the heart of St Helens. The village green (England's second largest) lies a few yards...

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

Price per week £471 - £668

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


4 Carina is a modestly furnished, first floor apartment in a converted house which offers a great value break for families or a couple. Centrally located and just yards from the sh...

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

Price per week £472 - £533

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


Nestled in the stunning countryside on the south west coast of the Island with far reaching sea views over the Military Road, this gorgeously converted barn is the perfect holiday ...

  • Sleeps 4 + 2 cots
  • Regret no pets
  • Changeover Fri

Price per week £475 - £710

Choose from our exclusive collection at the best prices with real time availability.

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