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 165 Isle of Wight cottages for September
7 nights from £311
The Crows Nest
36702 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
The Crows Nest is a second floor apartment at the top of a Victorian property in the historic village of Seaview. A family looking for a convenient base from which to enjoy the Isl...
7 nights from £311
7 nights from £322
3 Kings House
35442 bedroom, rural self catering cottage near the beach in Bembridge, Isle of Wight.
Take a few steps up to the entrance and you will find yourself in 3 Kings House, a ground floor apartment in a small development. It is the perfect base for a couple or a family wi...
7 nights from £322
7 nights from £330
6 Sandlands
35612 bedroom, rural self catering apartment near the beach in Ryde.
6 Sandlands is a modest top floor apartment with a large, open plan living area, just a stroll away from Ryde's wonderfully sandy beaches, the canoe lake and the children's sand pa...
7 nights from £330
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
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 £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
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 £347
Hove To
37672 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight
Hove To is one of a small collection of bungalows located along the Seaview Duver. Situated on the corner, it benefits from a large decked area on two sides with a lovely outlook o...
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
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
Choose from our exclusive collection at the best prices with real time availability.
Exclusive cottage collections
Our calendars show live availability, so if your pick of dates are available, you can reserve them safe in the knowledge that they won’t get sold anywhere else.
It can be unpredictable using aggregator websites that collect up information from across multiple websites. Our website stands alone, so you know what to expect and what you will get, for the best price. You won’t find this collection of cottages anywhere else, so pick your perfect place to stay from our exclusive portfolio.