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 113 Isle of Wight cottages for September

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

7 nights from £257

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

7 nights from £257

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £300

1 bedroom self catering apartment with sea views in Seaview, Isle of Wight


This gorgeous top floor, one bedroom apartment has spectacular sea views over the rooftops across the Solent, and is just a few minutes from Seaview village and the beach. Newly d...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £300

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

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £274

2 bedroom self catering cottage near the beach in Seaview.


Located in a small waterside development on the edge of Seaview, 62 Buddleia Cottage is a pretty beach bungalow offering comfortable accommodation, for a couple or small family, in...

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £274

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  • 20% off

    21 Sep 2019 - 28 Sep 2019

    £342.55 £274.04

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

7 nights from £208

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


Cockleshells is one of the charming Salterns bungalows situated along the Seaview Duver within a short walk to the Yacht Club and Seaview Village. The new Owner has completely rede...

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

7 nights from £208

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  • 40% off

    21 Sep 2019 - 28 Sep 2019

    £347.00 £208.20

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

7 nights from £241

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


The Crows Nest is a second floor apartment at the top of a Victorian property in the historic village of Seaview. A family looking for a convenient base from which to enjoy the Isl...

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

7 nights from £241

View
  • 20% off

    27 Sep 2019 - 4 Oct 2019

    £300.95 £240.76

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

7 nights from £274

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


The perfect bolt-hole for families, 61 Drake Cottage is a comfortably furnished beach bungalow located in a small waterside development on the edge of Seaview. Just yards from the ...

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

7 nights from £274

View
  • 20% off

    21 Sep 2019 - 28 Sep 2019

    £342.55 £274.04

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

7 nights from £319

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 £319

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

7 nights from £319

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


Yardley is a charming Victorian cottage, set in the centre of the pretty sailing village of Seaview. The beach and local shops are only a few minutes from your doorstep making this...

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

7 nights from £319

View
  • 15% off

    20 Sep 2019 - 27 Sep 2019

    £375.11 £318.84

Choose from our exclusive collection at the best prices with real time availability.

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

7 nights from £320

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 £320

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

7 nights from £324

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


5 Sandpipers is a well-equipped, modern house set within a small development in the heart of Seaview. It offers comfortable accommodation for a couple or small family. The sitt...

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

7 nights from £324

View
  • 10% off

    27 Sep 2019 - 4 Oct 2019

    £360.51 £324.45

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