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. 

We have 11 Isle of Wight cottages for September

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £340

1 Harrow Cottages

4642

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


This charming first floor apartment is in Nettlestone, just up the hill from Seaview and within walking distance of the beach. Surrounded by countryside there are lovely views from...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £340

  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £650

Temperance

4812

1 bedroom, dog friendly apartment near the beach in Freshwater, Isle of Wight.


Just a few minutes' walk from idyllic Freshwater Bay, Temperance is a real gem. A stylish and spacious first floor apartment, unwind into blissful island life where just a short wa...

  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £650

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

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

7 nights from £900

East View Cottage

4727

2 bedroom self catering cottage near the beach near Freshwater, Isle of Wight.


Nestled at the end of a quiet unmade track, East View Cottage has lovely views across the neighbouring fields and has a large private garden. There is gated access at the front wit...

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

7 nights from £900

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

7 nights from £700

4 Landfall House

4315

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


Situated just a few steps from the beach, this ground floor apartment makes the most of its location with both the sitting-room and kitchen/diner to the front boasting wonderful se...

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

7 nights from £700

  • Sleeps 12 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1500

Woodlands

4594

6 bedroom self catering home with sea views in Seaview, Isle of Wight.


This simply stunning four-storey, six bedroom house is situated in the village of Seaview within a few minutes' walk to the beach. With sea views from the top floor bedroom, Woodla...

  • Sleeps 12 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1500

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £1575

Hillside

4789

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


A beautifully renovated house tucked away in The Close, just a few minutes from idyllic Seagrove Bay, Hillside is a truly wonderful place to base yourself on the Isle of Wight. Lig...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £1575

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1680

Harbour View

4731

4 bedroom self catering cottage with sea views in Ryde, Isle of Wight.


Escape to the Isle of Wight for a blissful coastal retreat at Harbour View, an impressive Grade II Listed townhouse with stunning sea views, spread over three floors, and with the ...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1680

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

7 nights from £2400

Elmscott

4664

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


This gorgeous family home, within a few minutes' walk to Yarmouth town centre, has not only lovely accommodation but an outdoor heated pool set in a stunning garden. With off stree...

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

7 nights from £2400

We are Gold accredited with the Green Tourism Business Scheme.

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

7 nights from £1000

1 Church House

4596

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


A simply stunning church conversion in Totland on the west coast of the Island and within walking distance to the beach, making this the perfect holiday destination. Beautifully co...

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

7 nights from £1000

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £1250

Saye House

4573

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


Just a few minutes from idyllic Seagrove Bay, Saye House has been stylishly renovated to a high standard offering a wonderful place to enjoy a well-earned rest on the Isle of Wight...

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £1250

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