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 112 Isle of Wight cottages for September
7 nights from £1045
The Shack
56341 bedroom, dog friendly holiday cottage with sea views in Cowes.
Overlooking the waters of the Solent, start your mornings on the front deck admiring the view whilst deciding how to spend your day. Instantly relax into your holiday and breathe i...
7 nights from £1045
7 nights from £1056
Driftwood
56132 bedroom dog friendly luxury retreat with private hot tub.
Whisk yourself away to this pretty retreat on the glorious Isle of Wight, perfect for couples and families and your four-legged companions who love to explore as much as you do, an...
7 nights from £1056
7 nights from £1056
Escape Away
56122 bedroom dog friendly luxury retreat with private hot tub
Close to the beach, a short drive from pretty Yarmouth and not far from the iconic Needles, Escape Away is the perfect luxury retreat to base yourself for a peaceful and relaxing h...
7 nights from £1056
7 nights from £644
Blakesley Cottage
55652 bedroom, dog friendly self catering cottage in Godshill, Isle of Wight.
Nestled in the very heart of the Isle of Wight's rolling countryside close to the quintessential English village of Godshill yet just a short drive away from the stunning beaches o...
7 nights from £644
Bagwich House
7 nights from £1829
7 nights from £2517
Tamarisk House
55164 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight.
If you are seeking the ultimate coastal getaway with more than a little exclusivity, look no further than this luxurious retreat in Seaview overlooking the beautiful Solent on the ...
7 nights from £2517
7 nights from £1864 *
Halland Rise
55004 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight.
Introducing, Halland Rise, a stunning detached house sleeping eight guests, nestled in Seaview, one of the Island's most sought-after villages. With a choice of hidden coves and lo...
7 nights from £1864 *
7 nights from £1683
Firestone Lodge
54944 bedroom, dog friendly holiday cottage near the beach near Ryde, Isle of Wight.
Set back from the road and only a short walk from the pretty tidal estuary at Wootton Creek, Firestone Lodge sets the scene for your luxury holiday with family, friends and your mu...
7 nights from £1683
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 £1887
Dar View
54584 bedroom self catering cottage near the beach in Bembridge, Isle of Wight.
If you are looking for a stylish, spacious, yet comfortable retreat which boasts a superbly sought-after location, welcome to Dar View. An exquisite 'New England' style holiday...
7 nights from £1887
7 nights from £960
Lower Buoys
54572 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
Looking for buried treasure and an Island adventure? Look no further than this super ground floor, luxuxy apartment in a premier destination in the heart of Seaview. Enjoy beachsid...
7 nights from £960