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 167 Isle of Wight cottages for September
The Holly
40983 bedroom self catering cottage near the beach in Shanklin, Isle of Wight
A gorgeous Victorian three bedroom house on the outskirts of Shanklin with a lovely secluded garden and a private swimming pool. Beautifully decorated throughout, the Owner has tak...
Price per week £380 - £995
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50% off
14 Sep 2018 - 21 Sep 2018
£760.02 £380.00
30 Seaview Bay
35493 bedroom holiday cottage near the beach in Seaview, Isle of Wight.
30 Seaview Bay is a lovely three bedroom apartment set over two levels, offering sea views from the master bedroom balcony. Doors from the sitting-room lead to a decked area and pr...
Price per week £399 - £577
23 Coastguard Cottage
35343 bedroom self catering cottage near the beach in Bembridge, Isle of Wight.
This gorgeous property is a stylishly converted coastguard cottage and really is a gem. Beautifully decorated throughout, in greys, blues and whites, it is an oasis of calm and has...
Price per week £416 - £680
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20% off
21 Sep 2018 - 28 Sep 2018
£519.49 £415.60
2 Sandpipers
35253 bedroom self catering cottage near the beach in Seaview.
This modern, well-presented town house is located in a small development in the centre of Seaview. A true home-from-home, 2 Sandpipers is perfect for a coastal break with the famil...
Price per week £417 - £606
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10% off
21 Sep 2018 - 28 Sep 2018
£463.33 £417.00
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 November). 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!).
25 Palmerston Road
35383 bedroom self catering cottage near the beach in Shanklin.
25 Palmerston Road is a bright, cheerfully decorated, family home and is one of our most popular properties. This property is a real find for a family looking for a home both close...
Price per week £427 - £596
Trafalgar
40573 bedroom self catering cottage near the beach in Seaview, Isle of Wight
Nestled in the heart of Seaview village this lovely ground floor apartment is a stone’s throw from the sea front and all the village amenities. Seaview is an idyllic Edwardian reso...
Price per week £435 - £695
Blackberries
35833 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
Set in the delightful sailing village of Seaview, Blackberries is a pretty, refurbished cottage which offers a peaceful escape for families, small groups or couples alike. Comforta...
Price per week £436 - £801
East Gull Sands
35953 bedroom self catering cottage near the beach in Seaview, Isle of wight.
East Gull Sands is an attached, comfortably furnished, beachfront holiday home in Seaview. Sitting right opposite the beach this property has sea views from the upstairs double bed...
Price per week £451 - £719
Lawn End
36173 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
A hidden gem tucked away on Bluett Avenue in the peaceful Victorian village of Seaview, Lawn End makes great use of accent colours in its interior decor presenting a beautiful holi...
Price per week £453 - £650
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10% off
21 Sep 2018 - 28 Sep 2018
£519.82 £467.84
4 Commodores Court
35533 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
The wow factor at 4 Commodores Court is the location; perched directly opposite the beach it has stunning views of the Solent from the front, and delightful rural and lakeside view...
Price per week £461 - £560
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.