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 £408

2 bedroom, rural self catering cottage near the beach in Brighstone, Isle of Wight


One of two beautifully converted barns right in the heart of the Island's Area of Outstanding Natural Beauty. Equipped and decorated to a high standard mixing the charming features...

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

7 nights from £408

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £408

2 bedroom, dog friendly self catering cottage in a rural setting close to Godshill, Isle of Wight


Bagwich Barn Cottage is located in a stunning setting within the grounds of the main house and with two other barns available for larger parties. A charming sun-room to the front o...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £408

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

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

7 nights from £412

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


Newlands is a charming detached cottage located just off the Green, in the picturesque village of St Helens. Its location is very peaceful yet within walking distance to the villag...

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

7 nights from £412

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

7 nights from £414

2 bedroom thatched self catering cottage with sea views in Seaview.


If the restorative power of the sea appeals to you, 1 Thatched Cottage, with its uninterrupted views is an ideal holiday home. This 19th century property combines old world charm w...

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

7 nights from £414

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

7 nights from £417

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


Fir Cottage is an attractive and contemporary conversion of a Victorian home, located right in the heart of St Helens. The village green (England's second largest) lies a few yards...

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

7 nights from £417

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £418

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


If you are looking for a traditional cottage, look no further than Blakes Barn. Constructed from Island stone, the charm starts outside Blakes Barn with the beautiful brick work, t...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £418

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

7 nights from £434

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


If you're looking for a property that's practically on the beach, then this is it! 1 Starboard House perches just opposite the beach in central Seaview and enjoys uninterrupted sea...

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

7 nights from £434

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £457

2 bedroom, rural self catering apartment near Ventnor, Isle of Wight


Situated on the south coast of the Island, Sea Thrift is a pleasant ground floor apartment set in the ground of lovely gardens. With two delightful double bedrooms, both with en su...

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £457

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

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

7 nights from £459

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


Located in the cosmopolitan town of Ventnor in a Victorian town house, Seascape is a modern two bedroom apartment with spectacular sea views along the coastline. It offers contempo...

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

7 nights from £459

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

7 nights from £464

2 bedroom, dog friendly holiday apartment with sea views in Ventnor, Isle of Wight.


Gilmerton is a charming and spacious apartment, beautifully decorated, and located on the outskirts of the vibrant town of Ventnor. The house is built into the hill so this first f...

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

7 nights from £464

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