Holiday cottages for August on the Isle of Wight

Summer is here and it's time to let your hair down. For something a bit different this August, gather your loved ones and enjoy the holiday of a lifetime on the Isle of Wight. Be it for a weekend, two weeks or even a month, the choices are endless for the perfect break. Head to the island to see all there is on offer, and let the delicate sea breeze float your worries away.Read more

The Isle of Wight is an island full of adventure and when August rolls around, there is no better time to explore. Grab your sunglasses, don your t-shirt and shorts and head out into the great outdoors. There are miles of coast paths to explore, beaches to play on and pubs ready to welcome you afterwards with a cool beverage. Whether you are travelling solo or have a big party in tow, we have cottages of all shapes and sizes to accommodate your needs. Many of our self catering holiday cottages are dog friendly too, which means the whole family can enjoy an August break on the Isle of Wight.

Isle of Wight Holiday Cottages Available in August

Whatever you are looking for to take your holiday from great to fantastic, whether it be gorgeous sea views, a luxurious hot tub, private garden or something else, our portfolio will provide you with 29 of the highest quality cottages on the Isle of Wight.  

To ensure that you have the best holiday possible, at Classic Cottages we handpick all of our properties. Every cottage is personally inspected to meet exacting standards and each is fully equipped, from bed linens right down to the last teaspoon. Everything is taken care of so you don't need to worry about a thing. The most difficult decision? Which cottage to choose.

We have 29 Isle of Wight holiday cottages available in August

  • Sleeps 4
  • Regret no pets
  • Changeover Sat

7 nights from £649

1 Starboard House

3507

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


If you're looking for a property that's practically on the beach, then this is it! 1 Starboard House perches just opposite the beach in the centre of Seaview village and enjoys uni...

  • Sleeps 4
  • Regret no pets
  • Changeover Sat

7 nights from £649

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

7 nights from £720

The Pigsty

4538

2 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.


The Pigsty is a detached barn with parking for two cars and two private seating areas alongwith a spacious communal area. There are two bedrooms, a double and a twin, each beau...

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

7 nights from £720

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

7 nights from £745

Winkle Cottage

4395

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


This gorgeous terraced cottage, situated in the Conservation Area of the old town of Cowes, is just a few minutes walk from the centre of town, offering the perfect family holiday ...

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

7 nights from £745

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

7 nights from £936

The Clock House

4559

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


This beautifully decorated converted former stable, in the grounds of the Old Rectory in Yaverland just outside Bembridge, is a real gem. The owner has created a stylish and indivi...

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

7 nights from £936

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

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

7 nights from £1140

White Cottage

4892

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


Perfectly situated just a short drive from the delights of Ryde on the Isle of Wight, White Cottage is a beautifully furnished family holiday abode with a captivating garden to enj...

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

7 nights from £1140

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £1250

The Retreat

3741

2 bedroom, rural self catering cottage with sea views in St Helens, Isle of Wight.


Set in an idyllic location by the water’s edge on St Helens Duver, The Retreat offers stunning accommodation for a family holiday on the Island. There's beautiful living space ...

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £1250

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

7 nights from £1330

Sea Lights

4967

2 bedroom self catering apartment with sea views in Cowes, Isle of Wight.


Situated close to the beating heart of world-famous Cowes, lies the pretty coastal village of Gurnard. This handsome coastal ground floor apartment, comfortably sleeps four within ...

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

7 nights from £1330

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

7 nights from £975

Old Railway Cottage

3990

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


This charming cottage is tucked away down an unmade road just off Bembridge Harbour, within walking distance of Bembridge village centre. The front and rear gardens of Old Railway ...

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

7 nights from £975

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1406

Underwood Cabin

4995

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


Nestled in the beautiful grounds of St Hubert's Lodge and surrounded by tranquil woodlands and green pastures, Underwood Cabin is a delightful island retreat, perfectly situated in...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1406

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

7 nights from £1573

Old Bembridge House

4791

3 bedroom, dog friendly holiday cottage near the beach in Bembridge.


Tucked away on an unmade track just a few yards from the sea and Bembridge Yacht club, this wonderful Classic Cottage has all the makings of a perfect holiday idyll. Laid across th...

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

7 nights from £1573

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