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 157 Isle of Wight cottages for September

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

7 nights from £471

2 bedroom self catering apartment with sea views in Ventnor.


With sea views from the terrace and fresh, modern décor throughout, 2 St Josephs is a holiday maker's home-from-home. It is the perfect get-away for a small family, a couple or two...

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

7 nights from £471

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

7 nights from £475

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


This is a wonderfully secluded property with a charming garden and spacious balcony, all within a few minutes from the idyllic Seagrove Bay in Seaview. There are several steps up t...

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

7 nights from £475

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £495

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


Originally the farm's milking parlour, this delightful cottage sleeping four is the perfect cottage to spend quality time together as a family in a stunning rural location. Located...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £495

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £495

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


Originally the farms milking parlour, Dairy Cottage is a light and airy ground floor cottage with plenty of charm throughout. With a double bedroom with pleasant views across the f...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £495

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

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

7 nights from £500

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


6 St Joseph’s has stunning panoramic sea views, which you can sit and admire from the balcony, living room and master bedroom! Ideally positioned between Bonchurch and Ventnor this...

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

7 nights from £500

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

7 nights from £500

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


With one of the best views on the Isle of Wight, 1 St Josephs is a superb ground floor apartment beautifully decorated throughout. The property has a large patio area spanning two ...

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

7 nights from £500

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

7 nights from £506

2 bedroom self catering apartment near the beach in Seaview.


A ground floor apartment set within a gated development, 2 Springfield Court enjoys use of eight acres of shared grounds, a heated outdoor swimming pool and tennis court. It would...

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

7 nights from £506

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

7 nights from £510

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


4 Carina is a modestly furnished, first floor apartment in a converted house which offers a great value break for families or a couple. Centrally located and just yards from the sh...

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

7 nights from £510

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

7 nights from £514

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


Venice Lodge is a Georgian cottage located in a quiet residential area of the popular seaside town of Ryde. This is a unique house that you will not soon forget. If you long for th...

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

7 nights from £514

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £721

2 bedroom, rural self catering cottage with sea views in St Helens, Isle of Wight.


Set in an idyllic location by the water’s edge on St Helens Duver, The Retreat offers stunning accommodation for a family holiday on the Island. The property offers beautiful livin...

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £721

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

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