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

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

7 nights from £652

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 £652

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £701

3 bedroom thatched, dog friendly cottage in Tolpuddle, Dorset.


This very pretty thatched cottage is in the tranquil historic village of Tolpuddle, surrounded by beautiful countryside and just 15 miles from the World Heritage Jurassic Coast. Wi...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £701

  • Sleeps 6
  • Dogs welcome
  • Changeover Fri

7 nights from £704

3 bedroom, dog friendly holiday cottage near Lyme Regis, Dorset.


Imagine spending a week in a fabulous former dairyman’s cottage with all mod-cons! This very stylishly furnished, yet quirky, semi-detached cottage is in the village of Morcombelak...

  • Sleeps 6
  • Dogs welcome
  • Changeover Fri

7 nights from £704

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  • 20% off

    22 Feb 2019 - 1 Mar 2019

    £689.33 £551.46

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £720

3 bedroom holiday cottage in Corfe Castle, Dorset.


You will be completely spoilt for choice in this stunning part of Dorset – along the Jurassic Coast and within very easy reach are Lulworth Cove and Durdle Door with their famous c...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £720

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  • 20% off

    23 Feb 2019 - 2 Mar 2019

    £703.01 £562.41

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £768

4 bedroom holiday cottage near the beach in Studland, Dorset.


The Isle of Purbeck is a stunning Area of Outstanding Natural Beauty between Poole and Swanage boasting one of the most spectacular coastlines in Dorset. Sunnyholme, an extremel...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £768

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £790

3 bedroom holiday cottage in Corfe Castle, Dorset.


Situated in the popular Dorset village of Corfe Castle, on the Studland peninsula, close to the coast, this Grade II Listed picture-book cottage enjoys views of the spectacular Nat...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £790

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

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

7 nights from £852

3 bedroom, dog friendly cottage near the beach in Christchurch.


Avon Beach, Christchurch Harbour, the New Forest National Park and the Jurassic Coast are all nearby to this recently renovated holiday bolthole. The cool shades of blue and the pl...

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

7 nights from £852

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1010

4 bedroom, dog friendly cottage with sea views in Lyme Regis, Dorset.


Escape to the coast and this fabulous cottage where you can watch the seascape change all day long. Just minutes from the harbour at Lyme Regis and its iconic Cobb, this Grade I...

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1010

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

7 nights from £1516

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

7 nights from £1516

View
  • 15% off

    22 Feb 2019 - 1 Mar 2019

    £1186.64 £1008.95

  • 10% off

    1 Mar 2019 - 8 Mar 2019

    £1043.20 £938.70

  • 10% off

    8 Mar 2019 - 15 Mar 2019

    £1043.20 £938.70

  • 10% off

    22 Mar 2019 - 29 Mar 2019

    £1147.52 £1033.20

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

7 nights from £1625

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

7 nights from £1625

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