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 137 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 137 self catering cottages available to rent in June on the Isle of Wight

4 bedroom, rural self catering cottage near the beach in Yarmouth, Isle of Wight


This beautiful house is set in several acres of garden on the outskirts of Yarmouth, just a few minutes walk to the water’s edge, a truly stunning holiday destination. The property...

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

Price per week £1750 - £2550

4 bedroom self catering cottage with sea views in Seaview, Isle of Wight


A spectacular waterfront three-storey house situated on Seaview duver with uninterrupted sea views from the kitchen/dining-room and the first floor balcony. Just a few steps from y...

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

Price per week £1800 - £2400

We’re here to help you find your perfect place to stay 7 days a week.

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


6 Seafield Terrace is a charming terraced cottage set in the pretty village of Seaview. With spacious accommodation spread over three floors, and the beach close at hand, it makes ...

  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £795 - £1169

5 bedroom self catering cottage near the beach in Ryde, Isle of Wight.


Middle Lodge is a gorgeous 1860s, stone-built, Victorian holiday home set in a mature enclosed garden on the edge of Ryde on the east of the island. The outside is charmingly perio...

  • Sleeps 9 + cot
  • Regret no pets
  • Changeover Sat

Price per week £907 - £1385

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


2 Little Cedars is a sleek and modern property, with a light and clean finish throughout. Split over three floors, and stylishly decorated with luxury furnishings, this delightful ...

  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £1138 - £1854

5 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight


This is a three-storey house right in the heart of Bembridge village, just opposite the picturesque village church and a few minutes' walk from the shops and restaurants. The prope...

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Sat

Price per week £1200 - £1750

4 bedroom, dog friendly holiday cottage near the beach in East Cowes, Isle of Wight.


Barton Manor Farmhouse is a beautifully refurbished, 150 year old property set in the delightful grounds of the Barton Estate, adjacent to English Heritage's Osborne House, former ...

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £1771 - £2665

5 bedroom, dog friendly holiday cottage with sea views in Wootton, Isle of Wight.


Creekside is a fabulous waterfront property that makes a wonderful choice of holiday home at any time of the year. This stunning detached house, set on the banks of Wootton Creek, ...

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £921 - £1351

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.

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


Swift Cottage is a gorgeous, comfortable Edwardian end-of-terrace property, spread over three levels with wooden flooring throughout the kitchen and dining area. The spacious dinin...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

Price per week £926 - £1303

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


Orchard House is a wonderful property for an extended family looking for a sprawling holiday home near the beach in Bembridge. The downstairs living areas are inviting - no doubt t...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £1027 - £1543

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