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
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 89 Isle of Wight cottages for September
7 nights from £1759 booking fees included
St Hubert's Lodge
60573 bedroom, dog friendly self catering cottage near Yarmouth.
Surrounded by tranquil countryside on the edge of the Isle of Wight National Landscape and close to the charming seaside island towns of Yarmouth and Cowes, St Hubert's Lodge is a ...
7 nights from £1759
7 nights from £853 * booking fees included
Grey Gulls
61594 bedroom dog friendly self catering cottage with sea views in Seaview.
This beautifully presented, semi-detached, three-storey townhouse is set in the sought-after village of Seaview, just a stone's throw away from stunning beaches with crystal clear ...
7 nights from £853 *
We’ve been raising the standards of self catering holidays since 1977.
Our family ethos
Tony and Clare Tregoning started the business back in 1977 and their dedication to quality and excellence is at the heart of everything we do. Tony is sadly no longer with us, but we still adhere to their original ethos of finding holiday homes we would like to stay in and have slowly grown the company to find the best picks of properties across the counties. Plus Clare still drops in to keep us on our toes.
As an independent, family-run company, we wouldn’t expect you to stay anywhere we wouldn’t want to stay ourselves. And we’re pretty picky. We want you to walk into your handpicked holiday home and say ‘wow’, sit back and relax.
7 nights from £650 booking fees included
Bay Cottage
61502 bedroom self catering cottage near the beach in Cowes.
Tucked away in the charming village of Gurnard on the northwest coast of the Isle of Wight, this cosy two bedroom cottage offers a relaxed coastal lifestyle, complete with a pretty...
7 nights from £650
7 nights from £914 * booking fees included
Little Field
61233 bedroom, dog friendly holiday cottage near the beach near Ryde.
Tucked away on a quiet road, Little Field has been lovingly built by the owners and offers guests a peaceful and tranquil retreat with oodles of space and modern living. Situated o...
7 nights from £914 *
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £646 booking fees included
Seascape
59442 bedroom self catering apartment with sea views in Ventnor, Isle of Wight.
Located in the cosmopolitan town of Ventnor within a Victorian townhouse, Seascape is a modern two-bedroom, ground floor, apartment with spectacular sea views overlooking the bay. ...
7 nights from £646
7 nights from £1211 booking fees included
Maybury
59913 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
Your dream coastal escape awaits in Seaview! Escape to elegant Maybury and stay in this beautifully styled home with sandy beaches and village amenities on your doorstep. This blis...
7 nights from £1211
7 nights from £1167 booking fees included
Sun Lodge
58534 bedroom, dog friendly holiday cottage with sea views in Ventnor.
Step back in time and immerse yourself in the historic charm of Ventnor at this elegant Isle of Wight retreat with mesmerising sea views and generous spaces for a truly relaxing fa...
7 nights from £1167
7 nights from £654 * booking fees included
48 Solent View
58283 bedroom self catering cottage with sea views in Seaview.
Just a short wander from the golden sands of Seagrove Bay and the quaint charm of Seaview village, this stylish holiday haven offers modern home comforts in an unbeatable location ...
7 nights from £654 *
7 nights from £741 booking fees included
Bentinck
57243 bedroom cottage near the beach in Ventnor.
With everything you could wish for on your doorstep for a blissful Isle of Wight holiday experience with family or friends, Bentinck is a great base to explore all that this Island...
7 nights from £741
7 nights from £1811 * booking fees included
Pepita
57195 bedroom, dog friendly holiday cottage with sea views in Seaview.
With breathtaking sea views and the beach only a few steps from the front door, two former coastguard cottages and the adjoining boathouse have been transformed into an island gem,...
7 nights from £1811 *
Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.
Towels and readymade beds
All of our cottages provide bed linen and towels as standard, with a change of bedding included for holidays of two weeks or more. You’ll also find a fresh change of towels for each week (for in the house only, please bring your own for the beach) and tea towels a-plenty.
The beds will be readymade and waiting for you on arrival so you can simply sink into comfort and relax straight into your holiday.
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.
