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 £268
West Flatlet
36921 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
West Flatlet is situated right in the heart of Seaview village and is perfect for couples looking for a coastal break. This small but cosy and comfortable first floor flat sits at ...
7 nights from £268
7 nights from £300
The Sail Loft
41071 bedroom self catering apartment with sea views in Seaview, Isle of Wight
This gorgeous top floor one bedroom apartment has spectacular sea views over the rooftops across the Solent and is just a few minutes from Seaview village and the beach. Newly dec...
7 nights from £300
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 £325
Little Barn Retreat
41871 bedroom, rural self catering cottage in Newport, Isle of Wight
This absolutely gorgeous barn conversion is the perfect place for a couple's holiday, located on the Durton Farm Estate in the centre of the Island. Lovingly refurbished by the own...
7 nights from £325
7 nights from £357
Berryl Mead View
39061 bedroom self catering cottage near Ventnor, Isle of Wight
Located in a rural village setting, Berryl Mead View is a delightful home from home cottage with plenty of space, well equipped throughout and extremely comfortable living room wit...
7 nights from £357
7 nights from £376
Sea Song
39401 bedroom self catering apartment near Ventnor, Isle of Wight
Sea Song is an attractive one bedroom, first floor apartment overlooking beautiful communal gardens and surrounded by woodland on the southernmost tip of the island. Perfect for ro...
7 nights from £376
7 nights from £435
The Battenburg Studio
36641 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.
This contemporary studio apartment enjoys a great location in Shanklin. With modern decor and open plan living, it makes a cosy retreat for a couple looking for a coastal break. Wi...
7 nights from £435
7 nights from £435
The Beatrice Studio
36661 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.
Located on the first floor of Shanklin Villa, a lovely Victorian property, this small studio apartment packs a punch despite its size. Enjoying beautiful sea views from its elevate...
7 nights from £435
7 nights from £660
The Cadogan Apartment
36671 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.
Sitting within a beautifully converted Victorian villa, The Cadogan Apartment offers a high standard of accommodation for a couple or lone traveller looking for a coastal break. Gu...
7 nights from £660
We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.
Quality Accredited Agency
Only the highest quality of accommodation is awarded Visit England accreditation. The assessment takes place over a few days and looks at all of our policies, practices and procedures, making sure we meet a five star standard for our guests.
We set our own standards above and beyond and we’re very proud of this accolade and all it represents.
7 nights from £343
62 Buddleia Cottage
35662 bedroom self catering cottage near the beach in Seaview.
Located in a small waterside development on the edge of Seaview, 62 Buddleia Cottage is a pretty beach bungalow offering comfortable accommodation, for a couple or small family, in...
7 nights from £343
7 nights from £660
The Worsley Apartment
36821 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.
Offering a high standard of accommodation, the Worsley Apartment is a ground floor apartment housed within Shanklin Villa, a beautifully converted Victorian building. With a separa...
7 nights from £660