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 10 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £1700

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


This is an absolutely stunning detached house situated along Ducie Avenue, a private unmade road leading to the beach, in the charming seaside village of Bembridge. Within a few mi...

  • Sleeps 10 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £1700

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1711

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


A truly amazing, contemporary home with views directly out to sea, in the popular sailing town of Cowes. Offering exceptional quality throughout the whole home this is a superb bas...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1711

  • Sleeps 12 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £1192

5 bedroom self catering home near the beach in Seaview, Isle of Wight.


A beautiful Edwardian villa, with evident period charm, West Ingle boasts sea views from almost every room. Spacious, light and airy, many original features have been retained. Bot...

  • Sleeps 12 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £1192

  • Sleeps 12 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1329

6 bedroom, rural self catering home with sea views in Seaview, Isle of Wight.


Bay House is an incredibly spacious and stylish Edwardian villa offering great sea views from many of its rooms. Lovingly refurbished throughout, the property is the ideal choice f...

  • Sleeps 12 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1329

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

  • Sleeps 12 + 3 cots in 3 properties
  • Changeover Fri

7 nights from £1408


Mattingley Farm is made up of three beautiful cottages, each sleeping up to four guests, and is the perfect getaway for a family or friends holiday. Dairy Cottage (3912) and Orchar...

  • Sleeps 12 + 3 cots in 3 properties
  • Changeover Fri

7 nights from £1408