Self-Catering Cottages in Dorset for September
See Dorset bathed in the late summer sunshine this September and enjoy the opportunity to unwind. September enjoys a slower pace with many of Dorset's summer crowds tapering off and the county truly relaxed under blue skies. Whether you are looking for a solo adventure, romantic retreat or catch up with friends in luxury accommodation, enjoy a dream holiday in a Classic cottage. Read more
From country to coast, make the most of Dorset's natural gems and patchwork of towns and villages this September. With life slowing down a gear as children go back to school and summer visitors head home, September is a wonderful time for a Dorset getaway. Walk, talk and explore by day and then when you are ready to turn in, open the door to your dream home-from-home. At Classic Cottages we know a thing or two about what makes holidays great and will always go the extra mile to make sure your whole experience is the best it can be. Across Dorset, our cottages are wide in variety and consistent in quality. Many are dog-friendly too, which is great news for your four-legged friend. Take a look at our 42 available cottages and secure your September retreat today.
Our exclusive ferry discounts will make your island trip with Classic plain sailing.
We have 42 Dorset cottages available in September
7 nights from £644
Ivy Cottage
41222 bedroom, dog friendly cottage in Cattistock near Dorchester, Dorset.
Imagine life in a tranquil Dorset village and Ivy Cottage is just the sort of place you may picture in your mind. Set in the midst of an Area of Outstanding Natural Beauty (now ren...
7 nights from £644
7 nights from £2296
The Old Manor House
41245 bedroom, dog friendly cottage close to the beach near Lyme Regis.
Less than half a mile from the World Heritage Jurassic Coast, The Old Manor House is a beautiful 16th Century, Grade II Listed house, full of character with a delightful enclosed g...
7 nights from £2296
7 nights from £2070
Buddlewall
39796 bedroom thatched, dog friendly home near Lyme Regis, South Devon.
Buddlewall is an historic east Devon farmhouse, in a beautiful hidden rural setting, a short drive inland from the spectacular World Heritage east Devon and Dorset Jurassic Coast. ...
7 nights from £2070
7 nights from £725
Tolpuddle Cottage
37523 bedroom thatched, dog friendly cottage in Tolpuddle, Dorset.
This pretty thatched cottage is in the tranquil historic village of Tolpuddle, just 15 miles from the World Heritage Jurassic Coast. An ideal base for a family holiday or perfect f...
7 nights from £725
7 nights from £662
The Chalet on the Beach
3351Chalet on the beach sleeping two in Lyme Regis, Dorset.
Imagine a holiday right on the seashore of a very special beach, relaxing on your verandah with a glass of something refreshing, watching the gentle waves at one of the most famous...
7 nights from £662
7 nights from £1428
Cobb Cottage
32434 bedroom, dog friendly cottage with sea views in Lyme Regis, Dorset.
Escape to the coast and this fabulous cottage where you can watch the seascape change all day long. Just minutes from the harbour at Lyme Regis and its iconic Cobb, this Grade I...
7 nights from £1428
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 £1092
Sandy Days
32153 bedroom, dog friendly cottage near the beach in Christchurch.
Avon beach, Christchurch Harbour, the New Forest National Park and the Jurassic Coast are all nearby to this holiday bolthole. The cool shades of blue and the plantation shutters e...
7 nights from £1092
7 nights from £545
Badgers Cottage
30141 bedroom, dog friendly cottage near Bridport, Dorset.
This pretty semi-detached cottage for two is nestled within an Area of Outstanding Natural Beauty (now known as National Landscapes) on West Hembury Farm. Badgers Cottage is an ...
7 nights from £545
7 nights from £869
Barn Owls Cottage
30153 bedroom, dog friendly cottage near Bridport, Dorset.
Barn Owls Cottage is a semi-detached cottage that has been converted from an 18th Century stone barn. Despite having stylish modern fittings, it has still retained much of its orig...
7 nights from £869
West Hembury Farm
7 nights from £1414
