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. 

We have 28 Isle of Wight cottages for September

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

7 nights from £340

1 Harrow Cottages

4642

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


This charming first floor apartment is in Nettlestone, just up the hill from Seaview and within walking distance of the beach. Surrounded by countryside there are lovely views from...

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

7 nights from £340

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £450

Little Barn Retreat

4187

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


This absolutely gorgeous barn conversion is the perfect place for a couple's holiday, located on the Durton Farm Estate in the centre of the Island. Lovingly refurbished by the own...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £450

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

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

7 nights from £503

50 Solent View

4144

2 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 ...

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

7 nights from £503

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

7 nights from £600

The Clock House

4559

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


This beautifully decorated converted former stable, in the grounds of the Old Rectory in Yaverland just outside Bembridge, is a real gem. The owner has created a stylish and indivi...

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

7 nights from £600

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £850

The Retreat

3741

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 l...

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £850

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

7 nights from £860

The Shack

4730

2 bedroom, dog friendly holiday cottage with sea views in Cowes, Isle of Wight.


The perfect holiday hideaway The Shack, overlooks the waters of the Solent so you can start the day sitting on the front deck with your morning coffee admiring the wonderful view. ...

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

7 nights from £860

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

7 nights from £900

East View Cottage

4727

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


Nestled at the end of a quiet unmade track, East View Cottage has lovely views across the neighbouring fields and has a large private garden. There is gated access at the front wit...

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

7 nights from £900

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £950

2 Sea Whispers

3978

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


This charming first floor apartment is laid over two floors and situated right in the heart of Seaview village, tucked away down a quiet side street called Rope Walk, so-called as ...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £950

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

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

7 nights from £525

2 Stanfield House

3531

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


This spacious and sunny first floor apartment is located right in the heart of Seaview village overlooking the High Street and within a few minutes' walk to the beach. Comfortably ...

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

7 nights from £525

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

7 nights from £550

Pandora Lodge

3642

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


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 £550

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