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 19 Isle of Wight cottages for September
7 nights from £479
The Cattle Byre
45352 bedroom, dog friendly self catering cottage near Brighstone.
The Cattle Byre has accommodation for three guests across two bedrooms, a double and a single. It has two private outdoor seating areas, the rear enclosed garden can only be access...
7 nights from £479
7 nights from £409
1 Starboard House
35072 bedroom, rural self catering cottage near the beach in Seaview, Isle of Wight.
If you're looking for a property that's practically on the beach, then this is it! 1 Starboard House perches just opposite the beach in the cenre of Seaview village and enjoys unin...
7 nights from £409
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 £450
Yardley
36972 bedroom, rural self catering cottage near the beach in Seaview, Isle of Wight.
Yardley is a charming Victorian cottage, set in the centre of the pretty sailing village of Seaview. The beach and local shops are only a few minutes from your doorstep making this...
7 nights from £450
7 nights from £461
50 Solent View
41442 bedroom self catering cottage near the beach in Seaview, Isle of Wight
This is a wonderfully secluded property with a charming garden and spacious balcony, all within a few minutes from the idyllic Seagrove Bay in Seaview. There are several steps ...
7 nights from £461
7 nights from £500
Myrtle Dene
45082 bedroom self catering cottage with sea views in Wootton, Isle of Wight.
With views across the creek from both the garden and the first floor balcony, Myrtle Dean is a charming holiday home. Situated midway between Ryde and Newport, Wootton Creek is a g...
7 nights from £500
7 nights from £540
The Pigsty
45382 bedroom, dog friendly cottage near the beach near Brighstone.
The Pigsty is a detached barn with parking for two cars and two private seating areas alongwith a spacious communal area. There are two bedrooms, a double and a twin, each beau...
7 nights from £540
7 nights from £540
The Stables
45372 bedroom, dog friendly self catering cottage near Brighstone.
The Stables is light and airy throughout with two bedrooms, a king-size double and a twin. The open plan living-room with kitchen and dining areas is warm and inviting, with doors ...
7 nights from £540
7 nights from £595
The Dairy
45362 bedroom, dog friendly cottage near the beach near Brighstone.
The Dairy is the largest of all four barns and is closest to The Cattle Byre. It has a spacious kitchen and dining area making it a social space for the family to gather and make p...
7 nights from £595
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 £574
The Barn
36633 bedroom, rural self catering cottage near the beach in Merstone, Isle of Wight.
The Barn, a linked country cottage with a rustic interior and some exposed wooden beams, is located on the outskirts of Merstone and just minutes from the quaint village of Godshil...
7 nights from £574
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15% off
26 Sep 2020 - 3 Oct 2020
£674.98 £573.73
7 nights from £625
Modwena
44683 bedroom self catering cottage near the sea in Yarmouth, Isle of Wight.
This gorgeous three bedroom cottage is in the picturesque town of Yarmouth just a few minutes' walk to the village centre and historic pier. Located on the west coast of the Island...
7 nights from £625