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 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1020

4 bedroom self catering cottage with sea views near Ventnor, Isle of Wight


This large detached house is situated in an elevated position as you enter the town of Ventnor with the most breath-taking views from virtually every room. The beautiful tiered gar...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1020

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1295

4 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.


Set within a converted Victorian villa, Eversley Apartment is a large, contemporary split level apartment. With modern furnishings, this property offers a luxury option for a coast...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1295

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £1350

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


This absolutely stunning barn conversion is a little slice of luxury just outside the village of St Helens, only a short stroll to the St Helens Duver, sand dunes, beach and the Ba...

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £1350

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1395

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


Cromwell Apartment is a high end, beautifully presented, first floor apartment in a Victorian villa in Shanklin. Not your average beachfront apartment, the Cromwell comes with a de...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1395

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1500

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


This pretty attached Victorian cottage sits in the grounds of the Priory Estate and comes with use of its many diversions. With 70 acres of grounds to explore, plus a stunning priv...

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1500

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £1500

4 bedroom self catering cottage with sea views in Seaview, Isle of Wight


A spectacular waterfront three-storey house situated on Seaview duver with uninterrupted sea views from the kitchen/dining-room and the first floor balcony. Just a few steps from y...

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £1500

View
  • 50% off

    21 Jan 2019 - 26 Jan 2019

    £960.00 £480.00

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

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £1600

4 bedroom, rural self catering cottage near the beach in Yarmouth, Isle of Wight


This beautiful house is set in several acres of garden on the outskirts of Yarmouth, just a few minutes walk to the water’s edge, a truly stunning holiday destination. The property...

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £1600

  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £723

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


6 Seafield Terrace is a charming, spacious terraced cottage set in the pretty village of Seaview. It would ideally suit a large family, several couples or a group of friends travel...

  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £723

  • Sleeps 9 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £821

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


Middle Lodge is a beautiful 1860s, stone-built, Victorian holiday home set in a mature enclosed garden on the edge of Ryde on the near-east side of the Island. It would be ideal f...

  • Sleeps 9 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £821

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1000

5 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight


This is a three-storey house right in the heart of Bembridge village, just opposite the picturesque village church and a few minutes' walk from the shops and restaurants. The prope...

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1000

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