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 52 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 52 Isle of Wight holiday cottages available in August

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

7 nights from £674

2 bedroom, dog friendly holiday cottage near the beach in St Helens, Isle of Wight.


Faithfull Cottage is a lovingly restored, pretty mid-terrace cottage which enjoys a rear garden and countryside views on the outskirts of St Helens. This comfortable cottage is set...

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

7 nights from £674

View
  • 15% off

    29 Jun 2019 - 6 Jul 2019

    £414.11 £352.00

  • 10% off

    13 Jul 2019 - 20 Jul 2019

    £561.07 £504.96

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

7 nights from £674

2 bedroom, rural self catering apartment near the beach in Ryde.


6 Sandlands is a modest top floor apartment with a large, open plan living area, just a stroll away from Ryde's wonderfully sandy beaches, the canoe lake and the children's sand pa...

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

7 nights from £674

View
  • 10% off

    22 Jun 2019 - 29 Jun 2019

    £433.31 £389.98

  • 10% off

    13 Jul 2019 - 20 Jul 2019

    £549.11 £494.20

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

7 nights from £704

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


The Lobster Pot is a comfortably furnished beach bungalow located in a small waterside development on the edge of Seaview and next to a nature reserve. This beach bolt hole has dec...

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

7 nights from £704

View
  • 10% off

    5 Jul 2019 - 12 Jul 2019

    £577.90 £520.11

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

7 nights from £730

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


4 Tollgate Cottage is located near Seaview on the Duver - a beach front area that is home to the stunning Hersey Nature Reserve. This cosy cottage would suit a small family or a co...

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

7 nights from £730

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

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

7 nights from £796

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

7 nights from £796

View
  • 15% off

    28 Jun 2019 - 5 Jul 2019

    £533.27 £453.28

  • 10% off

    12 Jul 2019 - 19 Jul 2019

    £649.33 £584.39

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

7 nights from £825

2 bedroom self catering cottage with sea views in Seaview.


North View is a wonderful holiday hideaway just on the outskirts of Seaview with sea views across the Solent from the kitchen/dining-room and first floor bedrooms. Set back from th...

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

7 nights from £825

View
  • 15% off

    28 Jun 2019 - 5 Jul 2019

    £500.03 £425.03

  • 10% off

    12 Jul 2019 - 19 Jul 2019

    £675.02 £607.51

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £842

2 bedroom, dog friendly self catering cottage in a rural setting close to Godshill, Isle of Wight


Bagwich Barn Cottage is located in a stunning setting within the grounds of the main house and with two other barns available for larger parties. A charming sun-room to the front o...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £842

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

7 nights from £857

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


Fir Cottage is an attractive and contemporary conversion of a Victorian home, located right in the heart of St Helens. The village green (England's second largest) lies a few yards...

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

7 nights from £857

View
  • 10% off

    12 Jul 2019 - 19 Jul 2019

    £668.21 £601.39

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £857

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


If you are looking for a traditional cottage, look no further than Blakes Barn. Constructed from Island stone, the charm starts outside Blakes Barn with the beautiful brick work, t...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £857

  • Sleeps 4 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £867

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


Nestled in the stunning countryside on the south west coast of the Island with far reaching sea views over the Military Road, this gorgeously converted barn is the perfect holiday ...

  • Sleeps 4 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £867

View
  • 15% off

    28 Jun 2019 - 5 Jul 2019

    £595.00 £505.75

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