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 17 available cottages and secure your September retreat today.

We have 17 Dorset cottages available in September

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £561 *

3 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...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £561 *

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £409

2 bedroom dog friendly holiday cottage near Bridport, Dorset.


The pretty Dorset village of Drimpton is set in lovely countryside a short drive inland from the stunning Jurassic Coast. This original school house has been converted into extreme...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £409

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

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

7 nights from £453

2 bedroom, rural holiday cottage near Shaftesbury, Dorset.


Dairyman’s Cottage is traditional yet contemporary, semi-detached and set on a south-facing terrace. The property has a welcoming feel, with a stunning open plan design downstairs,...

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

7 nights from £453

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  • 20% off

    26 Jul 2019 - 2 Aug 2019

    £915.00 £732.00

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £453

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


Beehive Cottage is a charming and cosy cottage for four, on a quiet lane opposite St Mary's church in the village of Puddletown. The village is surrounded by farmland, Thomas Hardy...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £453

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

7 nights from £471

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 £471

View
  • 10% off

    16 Aug 2019 - 23 Aug 2019

    £827.00 £744.30

  • 10% off

    23 Aug 2019 - 30 Aug 2019

    £827.00 £744.30

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £508

2 bedroom, rural self catering cottage near Beaminster, Dorset.


A stunning west Dorset location, amazing rural views and a truly luxurious property, Phoebes House and neighbouring property Lottie's Loft (2565) both hidden gems just a short driv...

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £508

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

7 nights from £522

2 bedroom self catering cottage near the sea near Weymouth, Dorset.


This comfortable semi-detached family home is on the edge of the countryside, yet only three miles from Weymouth with its sandy beaches and historic quay. A 20 minute walk takes yo...

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

7 nights from £522

View
  • 10% off

    5 Aug 2019 - 9 Aug 2019

    £686.25 £617.63

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

7 nights from £522 *

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


This beautiful barn conversion at the heart of a working dairy farm is just inland from Dorset's spectacular Jurassic Coast and its beaches. The rural setting will please all the f...

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

7 nights from £522 *

Choose from our exclusive collection at the best prices with real time availability.

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

7 nights from £483

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 £483

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

7 nights from £502

2 bedroom, rural cottage near the beach near Bridport, Dorset.


The Parlour is an excellent choice for a family, with French windows opening out onto an enclosed gravelled patio, comfortable accommodation for five guests – one of the three sing...

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

7 nights from £502

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