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 81 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 81 Isle of Wight holiday cottages available in August

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

7 nights from £950

2 bedroom holiday apartment with sea views in Seaview, Isle of Wight.


With uninterrupted views across the Solent from the balcony, this first floor apartment is the perfect seaside bolthole to while away the days relaxing with a good book, a glass of...

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

7 nights from £950

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

7 nights from £959

2 bedroom self catering apartment with sea views in Ventnor.


With sea views from the terrace and fresh, modern décor throughout, 2 St Josephs is a holiday maker's home-from-home. It is the perfect get-away for a small family, a couple or two...

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

7 nights from £959

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £1184

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. The property offers beautiful livin...

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £1184

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

7 nights from £1200

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


Beginning its life as accommodation for troops during the First World War, The Blue Beach House has undergone many transformations in its time until its present day status as a cha...

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

7 nights from £1200

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

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £735

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


1 The Saltings is a three-bedroom, lower ground floor apartment boasting a lovely beachfront location. It would ideally suit a family with children keen to enjoy the delights of th...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £735

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  • 20% off

    19 Apr 2019 - 26 Apr 2019

    £470.94 £376.75

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £806

2 bedroom self catering cottage at Island Harbour, near Newport.


Spring Tide is a delightful holiday cottage situated in a small development at Island Harbour Marina on the banks of the River Medina. The marina is set in a beautiful secluded val...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £806

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £827

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


4A Ship House, an attractive townhouse positioned right in the middle of Seaview, is perfect for a family looking for a coastal break. 'Ship shape' in presentation, the fantastic t...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £827

  • Sleeps 5 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £837

2 bedroom, dog friendly holiday apartment near the beach in Shanklin.


Park Lodge Annexe is a beautifully presented lower ground floor apartment within walking distance to the Rylstone Gardens and the Chine. The cliff path is a minute stroll away, lea...

  • Sleeps 5 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £837

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £898

3 bedroom self catering cottage near the beach in Brook.


September Cottage is an excellent, family-friendly holiday home with an expansive, attractive kitchen and good-sized kitchen, sitting and dining areas. It's easy to imagine curling...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £898

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £913

3 bedroom self catering apartment with sea views in Seaview, Isle of wight.


Elm Cottage is a stylish first floor apartment brimming with character and comfort. It would suit friends traveling together, a couple or a family. From the front courtyard to t...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £913

We’ve been raising the standards of self catering holidays since 1977.

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