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. 

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 158 Isle of Wight cottages for September

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


Flackstead is a unique eco-friendly house which has breath-taking and uninterrupted coastal views across Compton Bay towards the Needles. Flackstead combines the very best of conte...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £1890 - £2200

3 bedroom, dog friendly holiday cottage near the beach in Totland, Isle of Wight


Ashmead Cottage has been thoughtfully decorated throughout offering three lovely bedrooms and two modern bathrooms. The kitchen opens out onto a charming private decked-area with o...

  • Sleeps 7 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £437 - £650

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


This light, beautifully presented holiday home offers quality accommodation with wooden floors, whitewashed walls and interesting prints and furnishings lending splashes of colour ...

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

Price per week £535 - £784

4 bedroom, rural self catering cottage on the outskirts of Wootton, Isle of Wight


This gorgeous stone cottage is tucked away in the most idyllic and tranquil location, surrounded by fields and woodland, this is the perfect holiday setting to truly escape from it...

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

Price per week £670 - £995

3 bedroom, rural self catering cottage near the beach in Shanklin, Isle of Wight.


Montagu is a luxurious, upper ground floor apartment forming part of a converted Victorian villa, just seconds from the beach at Shanklin. With a private patio with sea views and a...

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

Price per week £995 - £1395

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


One of a handful of pretty pastel beach bungalows located in Salterns Village, Curlew Cottage is a small, exclusive development at the edge of Seaview that offers securew communal ...

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

Price per week £479 - £849

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

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


Large and modern, Skylark Cottage is one of the premium properties available at Salterns Village, an exclusive small gated development on the edge of Seaview. The village has a lov...

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

Price per week £479 - £849

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


A smart town house, with well presented accommodation for eight set over three floors, Lucaya offers a great space with a pretty enclosed rear patio and lawn for an extended family...

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

Price per week £532 - £777

4 bedroom self catering apartment near the beach in Seaview.


Crowsteps is on the first and second floor of a property tucked away in Seaview in a semi detached property. Boasting a stunning roof terrace with far reaching views over the Solen...

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

Price per week £563 - £829

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


This bright, spacious detached house, on a quiet lane is just a 10 minute walk from the beautiful beach at Seagrove Bay. Furnished to a high standard, with four good-sized bedrooms...

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

Price per week £599 - £869

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