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 19 Isle of Wight cottages for September

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £479

The Cattle Byre

4535

2 bedroom, dog friendly self catering cottage near Brighstone.


The Cattle Byre has accommodation for three guests across two bedrooms, a double and a single. It has two private outdoor seating areas, the rear enclosed garden can only be access...

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £479

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

7 nights from £409

1 Starboard House

3507

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 the cenre of Seaview village and enjoys unin...

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

7 nights from £409

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

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

7 nights from £450

Yardley

3697

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


Yardley is a charming Victorian cottage, set in the centre of the pretty sailing village of Seaview. The beach and local shops are only a few minutes from your doorstep making this...

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

7 nights from £450

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

7 nights from £461

50 Solent View

4144

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


This is a wonderfully secluded property with a charming garden and spacious balcony, all within a few minutes from the idyllic Seagrove Bay in Seaview. There are several steps ...

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

7 nights from £461

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

7 nights from £500

Myrtle Dene

4508

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


With views across the creek from both the garden and the first floor balcony, Myrtle Dean is a charming holiday home. Situated midway between Ryde and Newport, Wootton Creek is a g...

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

7 nights from £500

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

7 nights from £540

The Pigsty

4538

2 bedroom, dog friendly cottage near the beach near Brighstone.


The Pigsty is a detached barn with parking for two cars and two private seating areas alongwith a spacious communal area. There are two bedrooms, a double and a twin, each beau...

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

7 nights from £540

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

7 nights from £540

The Stables

4537

2 bedroom, dog friendly self catering cottage near Brighstone.


The Stables is light and airy throughout with two bedrooms, a king-size double and a twin. The open plan living-room with kitchen and dining areas is warm and inviting, with doors ...

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

7 nights from £540

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

7 nights from £595

The Dairy

4536

2 bedroom, dog friendly cottage near the beach near Brighstone.


The Dairy is the largest of all four barns and is closest to The Cattle Byre. It has a spacious kitchen and dining area making it a social space for the family to gather and make p...

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

7 nights from £595

We’ve been raising the standards of self catering holidays since 1977.

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

7 nights from £574

The Barn

3663

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

7 nights from £574

View
  • 15% off

    26 Sep 2020 - 3 Oct 2020

    £674.98 £573.73

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

7 nights from £625

Modwena

4468

3 bedroom self catering cottage near the sea in Yarmouth, Isle of Wight.


This gorgeous three bedroom cottage is in the picturesque town of Yarmouth just a few minutes' walk to the village centre and historic pier. Located on the west coast of the Island...

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

7 nights from £625

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