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 158 Isle of Wight cottages for September
Solent Peek
39653 bedroom, dog friendly holiday cottage near the beach in Freshwater, Isle of Wight
Welcome to Solent Peek, a lovely comfortable home in Totland on the West Coast of the Island. As the name suggests, there is sea view from the first floor master bedroom and it is ...
Price per week £495 - £695
Turnstone
38283 bedroom self catering cottage in East Cowes, Isle of Wight
Turnstone is a beautifully designed, newly built town house situated overlooking the River Medina on the north coast of the island and within walking distance of Osborne House. Fro...
Price per week £495 - £640
Don’t miss out; reserve your favourite 2019 holiday cottage for just £30
Reserve your 2019 holiday
Our portfolio gets better year after year, with all the old favourites and some stunning new additions, so get in there quick and reserve your preferred dates for only £30.
Pick a place close to the coast for that year-round holiday vibe, or book a holiday townhouse to be close to every convenience. Escape to the country for peace and quiet or take to the moors for walks through wide open spaces, we’ve got plenty of holiday cottages for you to choose from for next year.
Reserve next year's holiday in advance to give you peace of mind and put off paying your deposit till after this summer (5th October). That way you know your preferred dates are yours for the choosing and you can get on with enjoying the rest of this year's holiday (before looking forward to the next!).
5 Yar Quay
38383 bedroom self catering cottage with sea views in St Helens, Isle of Wight
With wonderful views over Bembridge Harbour and Brading Marshes, 5 Yar Quay is a charming three storey house in St Helens within walking distance of Bembridge Village. The sitting-...
Price per week £495 - £750
Old Railway Cottage
39903 bedroom self catering cottage near the beach in Bembridge, Isle of Wight
This charming cottage is tucked away down an unmade road just off Bembridge Harbour, within walking distance of Bembridge village centre. The front and rear gardens of Old Railway ...
Price per week £495 - £715
9 Crown Court
41693 bedroom self catering cottage with sea views in Cowes, Isle of Wight.
Right in the heart of the bustling sailing town of Cowes, 9 Crown Court offers great accommodation with a stunning roof terrace boasting uninterrupted views across the rooftops to ...
Price per week £500 - £725
3 Quay Rocks
35453 bedroom self catering apartment near the beach in Seaview.
Perched right on the waterfront opposite Seaview beach, 3 Quay Rocks has unrivalled views of the attractive seafront and beyond, out to the ships passing by on the Solent. The apar...
Price per week £510 - £690
Portholes
40073 bedroom self catering cottage near the beach in Seaview, Isle of Wight
Tucked away down a quiet side street in the idyllic village of Seaview, Portholes is a fantastic holiday home just minutes away from the sea. All within walking distance from your ...
Price per week £520 - £795
1 Barton Lodge
35023 bedroom, dog friendly cottage near the beach in East Cowes, Isle of Wight.
This truly lovely holiday home, with a wood-burner, is a great choice whatever the season. 1 Barton Lodge is a beautiful property which has been lovingly restored with your comfort...
Price per week £544 - £753
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.
Little Bramley
40393 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight
A lovely three bedroom house in the heart of Seaview village within a few minutes walk to the seafront and Seaview Yacht Club. Beautifully decorated throughout with an open plan li...
Price per week £550 - £795
Willow Tree Lodge
39493 bedroom self catering cottage in Whitwell, Isle of Wight
Set in the rural village of Whitwell less than three miles outside of Ventnor, Willow Tree Lodge is a semi-detached bungalow offering comfort inside and out. Inside there are delig...
Price per week £566 - £867