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 106 Isle of Wight cottages for September
7 nights from £694
The Little Dairy Park Farm
56362 bedroom, dog friendly holiday cottage near Ryde, Isle of Wight.
This welcoming retreat is close to the pretty village of Seaview and the sandy beach at Ryde, and has the Isle of Wight Gin Distillery within walking distance. Thoughtfully present...
7 nights from £694
7 nights from £881 *
Escape Away
56122 bedroom self catering cottage near the beach in Freshwater.
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 £881 *
7 nights from £881 *
Driftwood
56132 bedroom, dog friendly holiday cottage near the beach in Freshwater, Isle of Wight.
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. Th...
7 nights from £881 *
Colwell Bay Cottages
7 nights from £1761
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7 nights from £2024
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 £2024
7 nights from £1856 *
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 lon...
7 nights from £1856 *
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
7 nights from £1782
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 £1782
7 nights from £768
Lower Buoys
54572 bedroom luxury apartment near the beach in Seaview, Isle of Wight.
Looking for buried treasure and an Island adventure? Look no further than this superb ground floor, luxury apartment in a premier destination, in the heart of Seaview. Enjoy beachs...
7 nights from £768
From £145 per night
Lazydays Hideaway
53811 bedroom glamping Yurt with sea views and an outdoor bath near Ventnor, Isle of Wight.
Welcome to Lazydays Hideaway, enjoying far reaching sea views across Reeth Bay and beyond and nestled on a hillside at the southerly point of the Isle of Wight. Whether you wan...
From £145 per night
Our property managers are local experts who handpick perfect places to stay.
Local experts
We scour the coast and country to winkle out bits worth sharing with you, the best properties in lovely locations. While we’re out and about, we gather together the best things to do so that you can start planning your holiday as soon as you’ve booked.
The ‘Explore Nearby’ tab on our cottage pages show what’s nearby along with relevant articles from our holiday guides from Notes and Stories, where you’ll find hand-written experiences of outings across the South and West, from dog-friendly pubs on the Isle of Wight to free things to do in south Devon and everything in between.
