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 158 Isle of Wight cottages for September

3 bedroom self catering cottage with sea views in Cowes, Isle of Wight.


Right in the heart of the bustling sailing town of Cowes, 9 Crown Court offers great accommodation with a stunning roof terrace boasting uninterrupted views across the rooftops to ...

  • Sleeps 6
  • Regret no pets
  • Changeover Sat

Price per week £575 - £625

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


Rose Villa is a little gem of a home in Yarmouth with its open plan kitchen and dining-table close to the doors to the garden, capturing the light nicely on a sunny day. Continuing...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £583 - £724

We’re here to help you find your perfect place to stay 7 days a week.

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


This charming cottage is tucked away down an unmade road just off Bembridge Harbour, within walking distance of Bembridge village centre. The front and rear gardens of Old Railway ...

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

Price per week £586 - £729

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


A fabulous holiday home, Trevenna is contemporary in style and many thoughtful touches are provided for guests. The interior is clean and fresh, there are wooden floors throughout ...

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

Price per week £591 - £742

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


Tucked away down a quiet side street in the idyllic village of Seaview, Portholes is a fantastic holiday home just minutes away from the sea. All within walking distance from your ...

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

Price per week £607 - £811

3 bedroom self catering apartment near the beach in Seaview.


Perched right on the waterfront opposite Seaview beach, 3 Quay Rocks has unrivalled views of the attractive seafront and beyond, out to the ships passing by on the Solent. The apar...

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

Price per week £610 - £704

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


1 Harbour Strand is a town house with jaunty decor, attractive furnishings and interesting prints, including some of the owners own artwork. It offers a games-room, with table-tenn...

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

Price per week £623 - £969

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


A seaside sanctuary, Shore House is a three-storey beautifully decorated house, with its own private heated swimming pool. Making the most of the far reaching views over the Solent...

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

Price per week £638 - £1015

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

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


This lovely and well-presented detached house is just moments away from the beautiful golden beaches of Ryde and mainland transport links, creating a perfect location for a base fo...

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

Price per week £650 - £875

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


The Barn, a linked country cottage with a rustic interior and some exposed wooden beams, is located on the outskirts of Merstone and just minutes from the quaint village of Godshil...

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

Price per week £665 - £865

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