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.
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
7 nights from £343
61 Drake Cottage
35652 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
The perfect bolt-hole for families, 61 Drake Cottage is a comfortably furnished beach bungalow located in a small waterside development on the edge of Seaview. Just yards from the ...
7 nights from £343
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20% off
25 May 2019 - 1 Jun 2019
£572.48 £457.98
7 nights from £346
The Lobster Pot
36722 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
The Lobster Pot is a comfortably furnished beach bungalow located in a small waterside development on the edge of Seaview and next to a nature reserve. This beach bolt hole has dec...
7 nights from £346
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20% off
24 May 2019 - 31 May 2019
£577.90 £462.32
7 nights from £347
Cockleshells
38152 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight
Cockleshells is one of the charming Salterns bungalows situated along the Seaview Duver within a short walk to the Yacht Club and Seaview Village. The new Owner has completely rede...
7 nights from £347
7 nights from £353
The Beach Retreat
36652 bedroom self catering cottage near the beach in Seaview.
This delightful, stylish seafront bungalow is located in a front row position with wonderful views of the Solent and the beach is practically on the doorstep. Days at the seaside, ...
7 nights from £353
Need more time? Reserve any cottage for up to 24 hours before booking.
24hr no commitment reservations
You can reserve your holiday dates on your favourite cottage for up to 24 hours. You might need to check with other guests in your party or simply consider whether this cottage is right for your holiday, either way we’re happy to give you the time to step away and mull over your options before paying a penny.
We’ll send you a reminder to see if you want it or not so you won’t lose out. Take time to think it over, you don’t have to rush your decision. Have a cup of tea and when you’re ready, hit the button to book your holiday and start looking forward to it.
7 nights from £355
Faithfull Cottage
36002 bedroom, dog friendly holiday cottage near the beach in St Helens, Isle of Wight.
Faithfull Cottage is a lovingly restored, pretty mid-terrace cottage which enjoys a rear garden and countryside views on the outskirts of St Helens. This comfortable cottage is set...
7 nights from £355
7 nights from £357
Smugglers’ Run
39452 bedroom, dog-friendly holiday cottage with sea views in East Cowes, Isle of Wight
Smugglers' Run is a waterside property overlooking the River Medina and across to the sailing town of Cowes. It would suit a family or a couple in need of a little extra space. ...
7 nights from £357
7 nights from £360
2 Bermuda
35172 bedroom self catering apartment with sea views in Seaview.
Not far from the sea you will find 2 Bermuda, a bright, neutrally decorated flat that is perfect for a family with children or a couple. The location is what makes this flat so spe...
7 nights from £360
7 nights from £372
53a Howgate Road
37492 bedroom, dog friendly apartment near the beach in Bembridge, Isle of Wight.
This two bedroom apartment in Bembridge is small but perfectly formed. Lovingly restored by the owners, 53a offers a perfect base for a family with a light and airy double bedroom ...
7 nights from £372
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10% off
24 May 2019 - 31 May 2019
£575.05 £517.55
7 nights from £373
4 Tollgate Cottage
41182 bedroom, dog friendly holiday cottage near the beach in Seaview.
4 Tollgate Cottage is located near Seaview on the Duver - a beach front area that is home to the stunning Hersey Nature Reserve. This cosy cottage would suit a small family or a co...
7 nights from £373
7 nights from £375
North View
41252 bedroom self catering cottage with sea views in Seaview.
North View is a wonderful holiday hideaway just on the outskirts of Seaview with sea views across the Solent from the kitchen/dining-room and first floor bedrooms. Set back from th...
7 nights from £375
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