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. 

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 37 available cottages and secure your September retreat today.

We have 37 Dorset cottages available in September

5 bedroom, dog friendly self catering cottage near Bridport, Dorset.


This beautiful stone farmhouse has something very special indeed – it comes with a 450 acre wildlife and nature reserve and a unique relationship with Dorset Wildlife Trust. Quite ...

  • Sleeps 9 + 2 cots
  • Dogs welcome
  • Changeover Fri

Price per week £845 - £1074

5 bedroom, dog friendly cottage near 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...

  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

Price per week £1516 - £2021

We are Gold accredited with the Green Tourism Business Scheme.

6 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. ...

  • Sleeps 12 + 2 cots
  • Dogs welcome
  • Changeover Fri

Price per week £1625 - £2223


These two delightful properties, set deep in Dorset's beautiful countryside, are the ultimate rural retreats! To set the scene, a long, unmade farm track leads to West Farm, where ...

  • Sleeps 6 in 2 properties
  • Changeover Fri

Price per week £963 - £1263


West Hembury Farm is situated in an Area of Outstanding Natural Beauty; a walker's paradise. Just four miles from the bustling market town of Bridport, and a short drive to the Wo...

  • Sleeps 8 + 3 cots in 2 properties
  • Changeover Fri

Price per week £1058 - £1393


This working farm on the edge of the historic village of Chideock stretches gently downhill to the Jurassic Coast where one of Dorset's most famous landmarks – Golden Cap – rises a...

  • Sleeps 9 + 3 cots in 3 properties
  • Changeover Sat

Price per week £1302 - £1705


Nestled into the hillside overlooking rolling green Dorset countryside, these three gorgeous lodges provide a holiday location where you can simply unwind from the moment you arriv...

  • Sleeps 13 + 3 cots in 3 properties
  • Changeover Fri

Price per week £1628 - £2121