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.

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 19 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.

Isle of Wight Ferry Booking With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing

We have 19 Isle of Wight holiday cottages available in August

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


West Flatlet is situated right in the heart of Seaview village and is perfect for couples looking for a coastal break. This small but cosy and comfortable first floor flat sits at ...

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

Price per week £399 - £420

View
  • 20% off

    22 Sep 2018 - 29 Sep 2018

    £262.50 £210.00

1 bedroom self catering apartment near Ventnor, Isle of Wight


Sea Song is an attractive one bedroom, first floor apartment overlooking beautiful communal gardens and surrounded by woodland on the southernmost tip of the island. Perfect for ro...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

Price per week £429 - £475

Don’t miss out; reserve your favourite 2019 holiday cottage for just £30

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

Price per week £475 - £500

1 bedroom, rural self catering cottage near Newport, Isle of Wight


Little Tremore Cottage is a charming annexe situated in the historic village of Shorwell, surrounded by peaceful and idyllic countryside; this is the place to be for a romantic, re...

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

Price per week £486 - £520

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 £578 - £640

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


Originally the farms milking parlour, Dairy Cottage is a light and airy ground floor cottage with plenty of charm throughout. With a double bedroom with pleasant views across the f...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £578 - £640

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 £605 - £695

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


4 Tollgate Cottages features an open plan living-room with wood-burning stove for cosy nights in and a door opening out to a decked area for the warmer nights. There is outdoor sea...

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

Price per week £628 - £730

View
  • 20% off

    22 Sep 2018 - 29 Sep 2018

    £373.10 £298.48

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

2 bedroom self catering cottage with sea views in Ventnor, Isle of Wight


Located in the cosmopolitan town of Ventnor in a Victorian town house, Seascape is a modern two bedroom apartment with spectacular sea views along the coastline. It offers contempo...

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

Price per week £653 - £780

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


One of two beautifully converted barns right in the heart of the Island's Area of Outstanding Natural Beauty. Equipped and decorated to a high standard mixing the charming features...

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

Price per week £735 - £850

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