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 1281 holiday cottages available in September
7 nights from £538
Kingfishers
60351 bedroom, dog friendly holiday cottage near Shaftesbury, Dorset.
Great care and attention has been put into this barn conversion, resulting in a truly cosy, yet spacious retreat for couples or solo travellers to enjoy. Located in Gillingham in n...
7 nights from £538
7 nights from £896 *
The Gatehouse
60332 bedroom self catering cottage in Malmesbury.
If ever a property was the epitome of luxury town living, then The Gatehouse is it. Located in the historic market town of Malmesbury it provides the perfect base for couples or fa...
7 nights from £896 *
Bluebell Cottage
178A beautiful cottage offering stunning views of the countryside and sea.
New for 2026! Bluebell Cottage is a beautifully presented one-bedroom retreat, perfect for a peaceful countryside escape with stunning views across open fields and out to sea. S...
Heron
177Stylish studio apartment located in an idyllic national glen.
Heron at Trail Lodge is a modern self-catering studio apartment set within the beautifully restored Silverdale Corn Mill, surrounded by the peaceful Silverdale Glen near Ballasalla...
Drakes
176Stylish studio apartment located in an idyllic national glen.
Drakes at Trail Lodge is a modern self-catering studio apartment set within the beautifully restored Silverdale Corn Mill, surrounded by the peaceful Silverdale Glen near Ballasall...
7 nights from £643 *
3 Kelly's Gardens
60562 bedroom, dog friendly cottage near the beach in St Ives, Cornwall.
Tucked away in the very heart of St Ives, 3 Kelly's Gardens is a charming two bedroom terraced cottage and is the perfect spot for couples or families looking to soak up the town's...
7 nights from £643 *
7 nights from £1001
Rockfield Lodge
60543 bedroom, dog friendly self catering cottage near Battle.
Situated in beautiful grounds just outside the medieval town of Battle and a short drive from Hastings and St Leonards-on-Sea, this delightful lodge offers a spacious holiday abode...
7 nights from £1001
7 nights from £898 *
The Police House
60514 bedroom, dog friendly holiday cottage near the beach in Seaview.
Perfectly situated in the heart of the charming village of Seaview on the stunning east coast of the Isle of Wight, The Police House is a delightful, detached holiday home located ...
7 nights from £898 *
Each and every one of our cottages is fully equipped with everything you’ll need on holiday.
Fully equipped cottages
All of our cottages have a standard list of equipment that goes above and beyond. As well as fluffy towels and readymade beds, our bare minimum includes everything you’ll need and more, from plenty of teaspoons to added extras such as gravy boats so no matter where you stay, you’ll be able to make your favourite home-cooked dishes.
Each inventory is regularly checked and counted so you won’t be stuck without a ladle and can leave your hairdryer at home, plus you’ll find a starter set of toiletries and cleaning products so you can get on with your holiday.
7 nights from £925
Darling Chestnut
60091 bedroom self catering cottage near Helford, West Cornwall.
Resting under the ancient chestnut tree, not far from the oak-lined banks of the Helford, this beautifully converted detached barn has been curated into a dreamy retreat for two lu...
7 nights from £925
7 nights from £1167
Starry Skies
60082 bedroom self catering cottage near Helford, West Cornwall.
Hidden away near the serene waters of the Helford River lies this thoughtfully renovated barn conversion and wild spa, where every detail has been crafted with care. From the soft-...
7 nights from £1167
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.
