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 20 available cottages and secure your September retreat today.

We have 20 Dorset cottages available in September

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £405

1 bedroom, rural holiday cottage near Dorchester, Dorset.


Dorset’s World Heritage Jurassic Coast is close to this comfortably furnished, single-storey, spacious cottage. Set within the grounds of the Owner’s home, The Stables is self-cont...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £405

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

7 nights from £409

1 bedroom, dog friendly self catering cottage near Sherborne, Dorset.


This cosy, compact, delightful bolthole for two is set in a wonderfully tranquil hamlet in north Dorset with village shops and a choice of two pubs within two miles. Built in lo...

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

7 nights from £409

Need more time? Reserve any cottage for up to 24 hours before booking.

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £411

1 bedroom, dog friendly cottage near the beach near Bridport, Dorset.


The Linhay is a tucked away single-storey retreat – and an ideal base for exploring the wonderful coastline. The cottage nestles alongside the barns, with a fully enclosed gravel c...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £411

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £416 *

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


Beehive Cottage is a charming and cosy cottage on a quiet lane opposite St Mary's church in the village of Puddletown. Surrounded by farmland, the pretty village is nestled in the ...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £416 *

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £455

2 bedroom thatched, dog friendly cottage near Beaminster, Dorset.


A gorgeous, chocolate-box cottage that is the ideal escape, nestled in the heart of one of Dorset's picturesque villages. Just a stone's throw from the lovely local pub, Wayside Co...

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £455

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

7 nights from £483

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


This pretty, detached former coach house is in beautiful rural Dorset, and within easy reach of the stunning World Heritage Jurassic coastline. The Old Coach House has a spaciou...

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

7 nights from £483

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £534

2 bedroom holiday cottage near Bridport, Dorset.


Close to Dorset's spectacular Jurassic Coast, the popular market town of Bridport and the harbour and beach at West Bay, this cottage has stunning views of the gentle Dorset countr...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £534

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £585

2 bedroom, rural holiday cottage near Shaftesbury, Dorset.


Located in an Area of Outstanding Natural Beauty, Hatts Farm is a working farm set in 150 acres on the Dorset and Wiltshire border. Dairyman's Cottage is traditional yet contempora...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £585

We are Gold accredited with the Green Tourism Business Scheme.

  • Sleeps 7 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £795 *

4 bedroom, dog-friendly cottage with sea views near Bridport, Dorset.


Snuggled into the hillside with Golden Cap behind, The Guardhouse stands watch over this stunning part of the Jurassic Coast at Seatown, with sea views from the master bedroom and ...

  • Sleeps 7 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £795 *

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £492

3 bedroom holiday cottage near Bridport, Dorset.


This sunny south-facing cottage enjoys a quiet rural position on the edge of the beautiful village of Netherbury, a short drive from the beaches and cliffs of the World Heritage Ju...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £492

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