Self-Catering Cottages in Dorset for September

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 33 available cottages and secure your September retreat today.

We have 33 Dorset cottages available in September

Bluebells is a 2 bedroom, dog friendly cottage in walking distance of Bridport, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £719

Bluebells

5624

2 bedroom, dog friendly cottage in walking distance of Bridport, Dorset.


Tucked away in a quiet location, yet just a stone's throw from bustling Bridport and the Jurassic Coast, you will find Bluebells. Situated at the end of a pretty row of cottages, t...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £719

The Old Dairy is a 2 bedroom, dog friendly cottage near Wimborne Minster, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1053

The Old Dairy

5551

2 bedroom, dog friendly cottage near Wimborne Minster, Dorset.


Situated within the southern neolithic ring of Knowlton Church and Earthworks and perfectly positioned under a Dark Sky Reserve, is The Old Dairy; a stylish and modern conversion t...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1053

The Gardens is a 2 bedroom, dog friendly cottage in historic Sherborne, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £701

The Gardens

5406

2 bedroom, dog friendly cottage in historic Sherborne, Dorset.


From the rolling hills of the Dorset countryside to the beautiful historic streets of Sherborne and down to the Jurassic Coast, explore it all whilst staying at The Gardens. This c...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £701

Pippins is a 3 bedroom, dog friendly character cottage near Beaminster, Somerset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £607

Pippins

5360

3 bedroom, dog friendly character cottage near Beaminster, Somerset.


Pippins is a picture postcard country cottage nestled in the charming Somerset village of North Perrott - not far from the Dorset border. This cosy home can cater for all of the fa...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £607

Seymour Barn is a 2 bedroom, dog friendly barn conversion in Bridport, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1135

Seymour Barn

5314

2 bedroom, dog friendly barn conversion in Bridport, Dorset.


With the bustling market town of Bridport within striking distance, this beautiful barn conversion is the perfect home-away-from-home. A delightful spot to explore all the beauty a...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1135

Ginny's Barn is a 2 bedroom, character cottage close to the Jurassic Coast, near Bridport, Dorset.
  • Sleeps 3
  • No pets
  • Changeover Fri

7 nights from £729

Ginny's Barn

5276

2 bedroom, character cottage close to the Jurassic Coast, near Bridport, Dorset.


Find your 'Far from the Madding Crowd' moment in the beautiful west Dorset countryside with a stay at Ginny's Barn. This quaint cottage is set in the grounds of the owners' home an...

  • Sleeps 3
  • No pets
  • Changeover Fri

7 nights from £729

Quince Cottage is a 3 bedroom, dog friendly cottage close to the beach near Bridport, Dorset.
  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £748

Quince Cottage

5190

3 bedroom, dog friendly cottage close to the beach near Bridport, Dorset.


With the World Heritage Jurassic Coast within one mile's walk, Quince Cottage is a welcoming home in the pretty West Dorset village of Chideock. This charming home is the perfect l...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £748

Woodville Cottage is a 3 bedroom, dog friendly home near the beach in Lyme Regis.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Wed

7 nights from £1380

Woodville Cottage

5151

3 bedroom, dog friendly home near the beach in Lyme Regis.


Woodville Cottage is a pretty and charming property, an annexe to a Grade II Listed Georgian building. Hidden away from the hustle and bustle of the elegant seaside town of Lyme Re...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Wed

7 nights from £1380

Our guests rate us 4.8/5 on Feefo, the independent review site.

Bay Tree Cottage is a 3 bedroom, dog friendly cottage near Bridport, Dorset.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £790

Bay Tree Cottage

4835

3 bedroom, dog friendly cottage near Bridport, Dorset.


Situated in a sleepy west Dorset village, just a short drive from the spectacular Jurassic Coast, you will find this pretty terraced cottage. Bay Tree Cottage offers all the deligh...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £790

The Old Dairy is a 2 bedroom, dog friendly former milking parlour near Blandford Forum, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £691

The Old Dairy

4740

2 bedroom, dog friendly former milking parlour near Blandford Forum, Dorset.


This former milking parlour that served the local farm has been beautifully converted into a fabulous holiday home. Situated in a picturesque Dorset village that is full of charact...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £691

Loading more