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.
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 163 Isle of Wight cottages for September
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...
Price per week £250 - £315
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 ...
Price per week £252 - £315
We are Gold accredited with the Green Tourism Business Scheme.
Green Tourism Business Scheme
As a company, we look across our business and try to make sustainable changes and decisions. From using recycled paper in our printers to putting in measures for using less energy in our offices, we keep an eye on our impact on the environment.
Beyond our offices, we have passed on the same ethics to our holiday cottage owners by setting up our own Green Scheme that they can join. Each property has to tick off a certain number of actions to be included in the scheme, many of which go above and beyond the GTBS requirements.
Little Tremore Cottage
39261 bedroom, rural self catering cottage near Newport, Isle of Wight
Little Tremore Cottage is a charming annexe situated in the historic village of Shorwell, surrounded by peaceful and idyllic countryside; this is the place to be for a romantic, re...
Price per week £338 - £463
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...
Price per week £341 - £400
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...
Price per week £470 - £660
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...
Price per week £309 - £444
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20% off
4 Aug 2018 - 11 Aug 2018
£670.00 £536.00
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'll find yourself in 3 Kings House, a ground floor apartment in a small development. The property is just a short walk from Bembridge Ha...
Price per week £295 - £398
53a Howgate Road
37492 bedroom, dog friendly apartment near the beach near St Helens, 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 ...
Price per week £295 - £450
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.
The Crows Nest
36702 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
The Crow's Nest is a second floor apartment of a Victoria property in the historic village of Seaview. Simply furnished but with wonderful views over the village rooftops to the So...
Price per week £295 - £375
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20% off
3 Aug 2018 - 10 Aug 2018
£595.00 £476.00
35 Cross Street
35502 bedroom, dog friendly holiday cottage near the beach in Cowes, Isle of Wight.
35 Cross Street is a cute end of terrace townhouse with accommodation spread over three floors, and has a sunny, enclosed courtyard. Built at the turn of the century, and decorated...
Price per week £303 - £436