Holiday Cottages for September
September is around the corner and a holiday in a self-catering cottage is beckoning. With the last of the summer sunshine, warm sea temperatures from months of hot weather and the crowds starting to dwindle, September is a fantastic time to enjoy a holiday in a home-from-home. Solo retreat, family holiday or gathering with friends, our cottages provide an idyllic base from which to enjoy a perfect getaway. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 1313 holiday cottages available in September
7 nights from £856 booking fees included
New Mill
61912 bedroom, dog friendly holiday cottage near Bovey Tracey, Dartmoor.
Welcome to this rather unique holiday retreat. New Mill is a rather deceiving name for this Grade II Listed watermill, which boasts many stunning original features, lovingly preser...
7 nights from £856
Ballachrink Barn
222Ballachrink Barn is a beautifully presented self-catering holiday cottage located in the peaceful village of Glen Maye on the west coast of the Isle of Man, just south of Peel. ...
Reserve your 2027 holiday for just £40.00
Find out more
7 nights from £1071 booking fees included
Hillside View
62153 bedroom, dog friendly holiday cottage near Tavistock, Dartmoor.
Tucked away in the glorious Tamar Valley, Hillside View is a rather special holiday retreat where peace, beautiful countryside and the great outdoors are right on your doorstep. Wi...
7 nights from £1071
7 nights from £943 booking fees included
Box Cottage
62073 bedroom, dog friendly cottage near the beach in Croyde, Devon.
In the heart of the charming village of Georgeham, just two miles from the golden sands of Croyde Bay and one mile from beautiful Putsborough Beach, Box Cottage is perfectly placed...
7 nights from £943
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £964 booking fees included
Ruska
6209Luxury cabin for two with an outdoor bath, privately nestled in the Forest of Dean.
Sitting in the Gloucestershire countryside, this lakeside retreat for two offers a peaceful and romantic getaway. This gorgeous cabin has been lovingly handcrafted with luxury in m...
7 nights from £964
7 nights from £905 booking fees included
Goaf Cottage
62042 bedroom, dog friendly self catering cottage near Whitby.
In a county of hills, dales and sandy beaches, you will find the moors village of Glaisdale and nestled in a sleepy lane sits Goaf Cottage, an old farm building converted into a go...
7 nights from £905
Greystones at Ago's Leap
221Impressive Douglas home with private gardens and tennis court
Set along Quarterbridge Road in Douglas, Greystones is a striking and spacious home offering an impressive place to stay within easy reach of the Island's capital. Beautifully p...
Ballacosney Cottage
219Stylish Laxey cottage with private gym and sauna
Tucked away up a peaceful lane above Laxey, Ballacosney Cottage is a beautifully renovated retreat designed with relaxing island stays in mind. Fresh, modern and filled with natura...
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10% off
10 Oct 2026 - 26 Oct 2026
7 nights from £901 booking fees included
Rubena Cottage
62002 bedroom, dog friendly cottage near the beach in Port Isaac.
A mere hop, skip and a jump from the water's edge, this absolute gem of a cottage has been restored with exquisite care, creating a most desirable retreat that's perfect for warm s...
7 nights from £901
7 nights from £1067 booking fees included
St Peter's House
62022 bedroom self catering cottage in Gloucester.
Set within Gloucester Cathedral's grounds with a magnificent glimpse of the Cathedral spires from the impressive staircase, St Peter's House enjoys a truly amazing location. A hous...
7 nights from £1067
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.
The beaches are inviting, the sea's had all summer to warm up and the schools have gone back, so make the most of quieter scenes still drenched in warm sunlight and give yourselves something to smile about. With our range of self-catering cottages, guests of all ages will settle straight in. Whether you are looking for a cottage nestled in the heart of lush countryside, a seaside sanctuary affording spectacular sea views or a town hub offering access to lots of local amenities, we will help you pave the way to your dream holiday this September. Offering a wide range of facilities, from enclosed gardens with barbecues, to homes with private swimming pools to properties with games rooms for kids, let your imagination run wild thinking about all the possibilities for your holiday in a Classic cottage.
Holiday Cottages for September
At Classic Cottages we pride ourselves on marketing only the finest quality self-catering accommodation around. Combining the highest level of customer service with luxury cottages, we want your whole holiday to be the best it can be. Browse our portfolio for September and find your favourite now.
