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 150 Isle of Wight cottages for September

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

7 nights from £425

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


Located in a quiet side street just off the village green in St Helens, this cosy cottage offers great accommodation with a good sized garden, spacious decking and outdoor seating ...

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

7 nights from £425

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £432

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


10 Tollgate Cottages is a pastel coloured, beach bungalow set in a small gated development close to the waterfront. Clean, neutral decor and its close proximity to the beach make t...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £432

View
  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £431.72 £345.37

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

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £432

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


24 Tollgate Cottages is a comfortable property just a stone's throw away from the beach, and a short walk from the local shops and dining in Seaview village. Situated on a small de...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £432

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £432

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


27 Tollgate Cottages is one of a number of well presented, beachfront holiday bungalows situated in Salterns Village, a small gated development located opposite Seaview Duver and b...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £432

View
  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £431.72 £345.37

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £432

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


6 Tollgate Cottages is a bright and cheery cottage set in a small, gated development near the pretty village of Seaview. Close to the beach, local shops and bars, and with Cafe Blu...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £432

View
  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £431.72 £345.37

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

7 nights from £439

3 bedroom holiday cottage near the beach in Seaview, Isle of Wight.


30 Seaview Bay is a lovely three bedroom apartment set over two levels, offering sea views from the master bedroom balcony. Doors from the sitting-room lead to a decked area and pr...

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

7 nights from £439

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

7 nights from £449

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


1 Yarborough Cottage is a wonderfully quaint end of terrace property facing St Helens Green on the east side of the island, with far reaching views over Culver Downs. The owners ha...

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

7 nights from £449

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

7 nights from £451

3 bedroom self catering cottage near the beach in Shanklin.


25 Palmerston Road is a bright, cheerfully decorated, family home and is one of our most popular properties. This property is a real find for a family looking for a home both close...

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

7 nights from £451

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

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

7 nights from £475

3 bedroom self catering apartment near the beach in Seaview.


Pandora Lodge is a lovely ground floor apartment forming part of a larger Victorian property in central Seaview. With sea views from the sitting-room and large bay windows featured...

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

7 nights from £475

View
  • 20% off

    6 Apr 2019 - 13 Apr 2019

    £581.79 £465.43

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

7 nights from £483

3 bedroom self catering cottage near the beach in Seaview.


This modern, well-presented townhouse situated in a small development in the centre of Seaview would suit a family, a couple or several friends traveling together. It really is...

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

7 nights from £483

View
  • 10% off

    5 Apr 2019 - 12 Apr 2019

    £626.00 £563.40

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