Isle of Wight Retreats in September

Enjoying the best bits of the summer - bright sunshine, warm seas, blue skies - with fewer crowds to share it with, September is an idyllic month to visit the Isle of Wight. Across the island we have properties of all shapes and sizes, so whether you are looking for a solo stay, romantic getaway for two or family holiday with the dog, you are sure to find a wonderful cottage just right for you. Read more

Wander the coast paths, stroll along the prom, visit little towns and breathe in the fresh air, September has all the ingredients for a wonderful holiday on the Isle of Wight. Whether you are planning a holiday well in advance to draw out your summer or are looking for a spontaneous short break for a sense of adventure, secure a Classic cottage and look forward to doing as much or as little as you please. With all of our cottages handpicked onto our books, we make sure exacting standards are maintained so you can enjoy the best self-catering accommodation on the Isle of Wight. Pour through our list of available cottages and fall in love with our luxury portfolio. Your only problem? Choosing just one. 

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

We have 151 Isle of Wight cottages for September

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

7 nights from £650

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


This lovely and well-presented detached house is just moments away from the beautiful golden beaches of Ryde and mainland transport links, creating a perfect location for a base fo...

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

7 nights from £650

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

7 nights from £665

3 bedroom, rural self catering cottage near the beach in Merstone, Isle of Wight.


The Barn, a linked country cottage with a rustic interior and some exposed wooden beams, is located on the outskirts of Merstone and just minutes from the quaint village of Godshil...

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

7 nights from £665

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  • 15% off

    30 Mar 2019 - 6 Apr 2019

    £565.02 £480.27

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

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £675

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


Located on the corner of Ryde Road, Westbourne is a lovely property ideally placed for Seaview Village and the beach. The village amenities are just a few minute's stroll away and ...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £675

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

7 nights from £675

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


Tucked away in the heart of Seaview village, 6 Seaview House is a charming ground floor apartment within a few minutes’ walk of the beach. It has private parking for two cars and a...

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

7 nights from £675

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

7 nights from £683

3 bedroom self catering cottage near the beach in Seaview.


In a quiet position within a secluded courtyard in the village of Seaview, Raleigh Cottage is the perfect blend of old-world charm and contemporary comfort. It would suit a family ...

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

7 nights from £683

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  • 15% off

    29 Mar 2019 - 5 Apr 2019

    £683.44 £580.92

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

7 nights from £689

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


Bay Cottage is a lovely three bedroom detached property on the outskirts of Seaview village, located in Seagrove Manor Road, a quiet spot yet just a few minutes walk into the villa...

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

7 nights from £689

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

7 nights from £695

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


Primrose Cottage is a fully modernised and beautifully furnished Victorian three bedroom cottage situated just off the green in St Helens and offering everything you might need for...

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

7 nights from £695

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £700

3 bedroom, rural self catering cottage in Newport, Isle of Wight


This property is a truly idyllic cottage situated in the grounds of a farm, with stunning countryside views and a lovely garden. This is what you would describe as holiday heaven. ...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £700

We’re here to help you find your perfect place to stay 7 days a week.

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

7 nights from £740

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


Right in the heart of Seaview village, this semi-detached property has been completely renovated, with a Skandi theme, to offer a wonderful place to stay on the Isle of Wight. With...

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

7 nights from £740

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  • 10% off

    29 Mar 2019 - 5 Apr 2019

    £739.56 £665.61

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

7 nights from £760

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


Ledge View is a beautifully renovated semi-detached home just steps away from Forelands beach, lined with quirky beach huts, stretches of white sand, rock pools and an acclaimed ca...

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

7 nights from £760

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  • 10% off

    23 Mar 2019 - 30 Mar 2019

    £760.44 £684.39

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