Holiday Cottages for June on the Isle of Wight

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 102 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

We have 102 self catering cottages available to rent in June on the Isle of Wight

Firestone Lodge is a 4 bedroom, dog friendly holiday cottage near the beach near Ryde, Isle of Wight.
  • Sleeps 7 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1852

Firestone Lodge

5494

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


Set back from the road and only a short walk from the pretty tidal estuary at Wootton Creek, Firestone Lodge sets the scene for your luxury holiday with family, friends and your mu...

  • Sleeps 7 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1852

Dar View is a 4 bedroom self catering cottage near the beach in Bembridge, Isle of Wight.
  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1566

Dar View

5458

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


If you are looking for a stylish, spacious, yet comfortable retreat which boasts a superbly sought-after location, welcome to Dar View. An exquisite 'New England' style holiday...

  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1566

Lower Buoys is a 2 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
  • Sleeps 4
  • No pets
  • Changeover Sat

7 nights from £1112

Lower Buoys

5457

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


Looking for buried treasure and an Island adventure? Look no further than this super ground floor, luxuxy apartment in a premier destination in the heart of Seaview. Enjoy beachsid...

  • Sleeps 4
  • No pets
  • Changeover Sat

7 nights from £1112

Lazydays Hideaway is a 1 bedroom glamping Yurt with sea views near Ventnor, Isle of Wight.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

From £180 per night

Lazydays Hideaway

5381

1 bedroom glamping Yurt with sea views near Ventnor, Isle of Wight.


Welcome to Lazydays Hideaway, enjoying far reaching sea views across Reeth Bay and beyond and nestled on a hillside at the southerly point of the Isle of Wight. Whether you wan...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

From £180 per night

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

Weirside Cottage is a 2 bedroom, dog friendly holiday cottage near the beach near Yarmouth.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £996

Weirside Cottage

5320

2 bedroom, dog friendly holiday cottage near the beach near Yarmouth.


As pretty as a picture, feast your eyes on Weirside a stunning Grade II Listed cottage at the heart of the idyllic island village of Brighstone, just half mile from the sea and the...

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

7 nights from £996

Berry Cabin is a 2 bedroom, dog friendly, self catering cottage in Seaview, Isle of Wight.
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £509

Berry Cabin

5286

2 bedroom, dog friendly, self catering cottage in Seaview, Isle of Wight.


What a little cutie! Berry Cabin is a delightful bolthole for four guests and one well behaved doggy looking for some summer fun! Surrounded by Hersey nature reserve and countrysid...

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

7 nights from £509

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

7 nights from £1833

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 £1833

Forget Me Not Cottage is a 3 bedroom self catering cottage near the beach in Bembridge, Isle of Wight
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £906 *

Forget Me Not Cottage

5167

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


Welcome to the delightfully named Forget Me Not Cottage, a charming three bedroom getaway in the pretty coastal town of Bembridge. With its homely interiors and great location, thi...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £906 *

Leeway House is a 4 bedroom, dog friendly holiday cottage near the beach in Cowes, Isle of Wight
  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1757

Leeway House

5138

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


Renowned as home to the largest sailing regatta in the world, Cowes is a pretty seaport town on the north side of the Isle of Wight, with fabulous views over the Solent and a great...

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1757

The Drey is a 3 bedroom self catering cottage near the beach in Seaview, Isle of Wight
  • Sleeps 6
  • No pets
  • Changeover Fri

7 nights from £1125

The Drey

5139

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


Located in the grand building that is Springfield Court, guests staying in this lovely holiday home can take full enjoyment of the grounds during their stay. Comfortably furnished ...

  • Sleeps 6
  • No pets
  • Changeover Fri

7 nights from £1125

Be in the know… Sign up to our newsletter for holiday inspiration, offers and all things Classic.

Loading more