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 165 Isle of Wight cottages for September

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

7 nights from £360

2 bedroom self catering apartment with sea views in Seaview.


2 Bermuda is a lovely, neutrally decorated first floor apartment with wonderful views across the Solent, a balcony for al fresco drinks and a pretty garden. With both the beach and...

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

7 nights from £360

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

7 nights from £372

2 bedroom, dog friendly apartment near the beach in Bembridge, Isle of Wight.


This two bedroom apartment in Bembridge is small but perfectly formed. Lovingly restored by the owners, 53a offers a perfect base for a family with a light and airy double bedroom ...

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

7 nights from £372

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

7 nights from £373

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 £373

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

7 nights from £375

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 £375

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

7 nights from £375

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 £375

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £381

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


23 Tollgate Cottages is a comfortably furnished beach bungalow located in a small, gated waterside development on the edge of Seaview, within walking distance to the shops and cafe...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £381

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

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

7 nights from £388

2 bedroom self catering apartment near the beach in Ryde.


6 Pier View Court, perfectly located right on the seafront at Ryde, is a modern, well presented second floor apartment, tastefully decorated and furnished to a high standard. Relax...

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

7 nights from £388

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

7 nights from £393

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 £393

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £399

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


A barn conversion in a rural setting, you'll enjoy a feeling of peace from the moment you step inside this lovely retreat, with its exposed beams and rustic decor. Sitting within t...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £399

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £399

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


A barn conversion, in a rural setting, with a welcoming, rustic feel to it, 1 Bagwich Barn offers an ideal base in the middle of the The Isle of Wight, from which to explore north ...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £399

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