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 151 Isle of Wight cottages for September

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

7 nights from £483

3 bedroom self catering cottage near the beach in Seaview.


This modern, well-presented townhouse situated in a small development in the centre of Seaview would suit a family, a couple or several friends traveling together. It really is...

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

7 nights from £483

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

7 nights from £503

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


Set in the delightful sailing village of Seaview, Blackberries is a pretty, refurbished cottage which offers a peaceful escape for families, small groups or couples alike. Comforta...

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

7 nights from £503

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

7 nights from £505

3 bedroom self catering apartment with sea views in Seaview.


They say location is everything, and this property does not disappoint! Situated on the first floor, 2 Quay Rocks is a light-filled, modestly furnished apartment with a balcony, of...

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

7 nights from £505

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

7 nights from £510

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


Nestled in the heart of Seaview village, this lovely ground floor apartment is a stone's throw from both the coastline and village amenities, in fact it is just steps away from a f...

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

7 nights from £510

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

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

7 nights from £521

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


Merries is a traditional beachside bungalow conveniently situated between Puckpool Park and Seaview village centre. It would suit a family wanting a convenient coastal holiday base...

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

7 nights from £521

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

7 nights from £528

3 bedroom self catering apartment near the beach in Seaview.


With a comfortable interior, an unbeatable location, manicured grounds and the beach within easy reach, 3 Springfield Court has it all. This delightful holiday home would suit a fa...

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

7 nights from £528

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

7 nights from £530

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


East Gull Sands is an attached, comfortably furnished, beachfront holiday home in Seaview. Sitting right opposite the beach this property has sea views from the upstairs double bed...

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

7 nights from £530

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

7 nights from £530

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


This gorgeous property is a stylishly converted coastguard cottage and really is a gem. Beautifully decorated throughout, in greys, blues and whites, it is an oasis of calm and has...

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

7 nights from £530

View
  • 20% off

    19 Apr 2019 - 26 Apr 2019

    £597.53 £478.02

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

7 nights from £531

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


A hidden gem tucked away on Bluett Avenue in the peaceful Victorian village of Seaview, Lawn End makes great use of accent colours in its interior decor presenting a beautiful holi...

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

7 nights from £531

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £561

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


Welcome to Solent Peek, a lovely comfortable home in Totland on the West Coast of the Island. As the name suggests, there is sea view from the first floor master bedroom and it is ...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £561

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

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