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 51 available cottages and secure your September retreat today.

We have 51 Dorset cottages available in September

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 self catering cottage in Sherborne, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £729

The Gardens

5406

2 bedroom, dog friendly self catering cottage in 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 £729

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

7 nights from £607

Pippins

5360

3 bedroom, dog friendly holiday 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 self catering cottage in Bridport, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1135

Seymour Barn

5314

2 bedroom, dog friendly self catering cottage 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

Periwinkle Cottage is a 1 bedroom, dog friendly self catering cottage in Bridport, Dorset.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £428

Periwinkle Cottage

5258

1 bedroom, dog friendly self catering cottage in Bridport, Dorset.


Tucked away off one of Bridport's vibrant streets is Periwinkle Cottage, a beautiful home ready to welcome you for a fantastic stay. This gorgeous terraced retreat is the perfect p...

  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £428

Ginny's Barn is a 2 bedroom, self catering cottage near Bridport, Dorset.
  • Sleeps 3
  • No pets
  • Changeover Fri

7 nights from £729

Ginny's Barn

5276

2 bedroom, self catering cottage 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

We’ve been raising the standards of self catering holidays since 1977.

St Peter's Cottage is a 3 bedroom thatched, dog friendly cottage near Dorchester, Dorset.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1077

St Peter's Cottage

5135

3 bedroom thatched, dog friendly cottage near Dorchester, Dorset.


Dating back to the early 17th Century, this picture perfect, Grade II Listed thatched cottage sits in the heart of a rural Dorset village. Recently renovated by the owners, St Pete...

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

7 nights from £1077

Park Farm Byre is a 3 bedroom, dog friendly holiday cottage near Dorchester, Dorset.
  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £903

Park Farm Byre

4956

3 bedroom, dog friendly holiday cottage near Dorchester, Dorset.


Tucked away in a rural location, you will find Park Farm Byre, a stylish retreat complete with hot tub and perfectly situated on a number of country and woodland walks. All on one ...

  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £903

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