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 155 Isle of Wight cottages for September

3 bedroom self catering apartment with sea views in Seaview, Isle of wight.


Elm Cottage is a stylish, spacious first floor apartment, brimming with quirky taste and character, in the sought after village of Seaview and it enjoys sea views across the roof t...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

Price per week £451 - £586

3 bedroom self catering cottage near the beach in Brook.


September Cottage is an excellent, family-friendly holiday home with an expansive, attractive kitchen and good-sized kitchen, sitting and dining areas. It's easy to imagine curling...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

Price per week £454 - £614

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

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


The location of 40 Trelawny Way, on a quiet residential road in Bembridge, belies its extravagant interior. For those looking for a family home with an interior decorated with arti...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

Price per week £517 - £673

3 bedroom, rural self catering apartment near the beach near Newport, Isle of Wight


This stunning barn conversion is located just outside the picturesque village of Chillerton, in the heart of the Island’s farming community between Newport and Chale. The outlook o...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

Price per week £561 - £709

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


An incredibly stylish three bedroom ground floor apartment ideally located a few minutes' walk from the village of Seaview and the beach. A lovely large entrance hall centrally fra...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

Price per week £612 - £790

3 bedroom, dog friendly self catering cottage in Ventnor.


This gorgeous stone cottage is nestled in a wonderful countryside location in the central south of the Island, a short distance from the coastal town of Ventnor. Situated at the en...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

Price per week £625 - £795

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


Dating back to 1863 and converted in 2011, this superb two-storey apartment is located on the outskirts of Shanklin. 10 Shanklin Manor has an elegant, monochrome interior and the u...

  • Sleeps 5
  • Regret no pets
  • Changeover Sat

Price per week £677 - £911

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


The Old Boat House is an attractive period cottage, set in a fantastic waterfront location on the edge of the beach at Seagrove Bay. This charming family home has been tastefully d...

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

Price per week £708 - £1565 *

* Includes 40% off for parties up to 5 + cot between 7 Sep and 28 Dec 2019. The annexe is excluded at the discounted rate

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.

3 Astra House is a comfortable first floor apartment within a converted Victorian House


3 Astra House is a comfortable first floor apartment within a converted, red brick Victorian house, located on a quiet residential no-through road in Seaview. Offering light and sp...

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

Price per week £410 - £536

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


27 Tollgate Cottages is one of a number of well presented, beachfront holiday bungalows situated in Salterns Village, a small gated development located opposite Seaview Duver and b...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £432 - £541

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