Holiday cottages for August on the Isle of Wight

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 95 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.

Our exclusive ferry discounts will make your island trip with Classic plain sailing.

We have 95 Isle of Wight holiday cottages available in August

Keepers Cottage is a 4 bedroom, rural self-catering cottage on the outskirts of Wootton, Isle of Wight
  • Sleeps 7 + cot
  • No pets
  • Changeover Fri

7 nights from £1216

Keepers Cottage

4070

4 bedroom, rural self-catering cottage on the outskirts of Wootton, Isle of Wight


This gorgeous stone cottage is tucked away in the most idyllic and tranquil location; surrounded by fields and woodland, this is the perfect holiday setting to truly escape from it...

  • Sleeps 7 + cot
  • No pets
  • Changeover Fri

7 nights from £1216

Inglefield is a 4 bedroom, dog friendly holiday cottage near the beach in St Helens.
  • Sleeps 7 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1254

Inglefield

5637

4 bedroom, dog friendly holiday cottage near the beach in St Helens.


This beautiful home close to Bembridge Harbour is a space to enjoy with family and friends. From exploring the bays and beaches to the rolling countryside and historic castles, Ing...

  • Sleeps 7 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1254

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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 £2092

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 £2092

Bentinck is a 3 bedroom cottage near the beach in Ventnor.
  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £1040

Bentinck

5724

3 bedroom cottage near the beach in Ventnor.


With everything you could wish for on your doorstep for a blissful Isle of Wight holiday experience with family or friends, Bentinck is a great base to explore all that this Island...

  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £1040

Lucaya is a 4 bedroom self catering cottage near the beach in Ryde, Isle of Wight.
  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £1137

Lucaya

3621

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


Welcome to Lucaya, a smart town house for eight set over three floors, a great space with a pretty enclosed rear patio and lawn, the ideal stay for a family looking for a seaside b...

  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £1137

House of Logs is a 4 bedroom, rural self catering cottage near the beach in Totland, Isle of Wight
  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1166

House of Logs

4225

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


House of Logs is a unique and stunning property located on the west coast of the Island, just a short walk from Widdick Chine and Totland Bay. Perfect for a peaceful holiday and do...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1166

St Albans House is a 4 bedroom self catering cottage with sea views near Ventnor, Isle of Wight
  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1203

St Albans House

3980

4 bedroom self catering cottage with sea views near Ventnor, Isle of Wight


This large detached house is situated in an elevated position as you enter the town of Ventnor, with the most breathtaking views from virtually every room. The beautiful tiered...

  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1203

Garsdon is a 4 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1229

Garsdon

3604

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


This lovely bright and spacious detached house located on a quiet lane in Seaview is just a ten minute stroll from the beautiful beach at Seagrove Bay. With a charming large enclos...

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

7 nights from £1229

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

Tangle Cottage is a 4 bedroom self catering cottage near the beach in Seaview.
  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1274

Tangle Cottage

5669

4 bedroom self catering cottage near the beach in Seaview.


Nestled at the end of Ryde Road, just a short walk from the beach and Seaview village, with off-street parking and a lovely large garden to the rear, semi-detached Tangle Cottage i...

  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1274

Pucks Oak is a 4 bedroom, dog friendly holiday cottage with sea views in Seaview.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1386

Pucks Oak

5698

4 bedroom, dog friendly holiday cottage with sea views in Seaview.


Within moments of the seafront at Seaview, with off-street parking and a lovely garden, semi-detached Pucks Oak is a great home-from-home to enjoy with friends and family. With the...

  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1386

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