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 36 available cottages and secure your September retreat today.

We have 36 Dorset cottages available in September

  • 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

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

7 nights from £473

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


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

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

7 nights from £473

  • 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 is a hidden gem just a short drive inland from the famous Jurassic Coast. This de...

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £508

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £510

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


Imagine life in a tranquil Dorset village and Ivy Cottage is just the sort of place you may picture in your mind. Set in the midst of an Area of Outstanding Natural Beauty, the cot...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £510

  • 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
  • 15% off

    21 Dec 2018 - 28 Dec 2018

    £744.51 £633.25

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

7 nights from £601

2 bedroom, rural holiday cottage near Bridport, Dorset.


Nestling in a picturesque valley a fifteen minute drive from the Jurassic Coast, Barbridge Cottage is close to beaches, walks, fossil hunting, country houses, gardens and lovely pu...

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

7 nights from £601

  • 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

View
  • 20% off

    21 Dec 2018 - 28 Dec 2018

    £796.00 £636.80

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

7 nights from £567

2 bedroom, rural holiday cottage near Shaftesbury, Dorset.


Semi-detached Hatts Barn is a contemporary, reversed level barn conversion on a wide south-facing terrace. The large en suite master bedroom and a twin bedded family room (the beds...

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

7 nights from £567

View
  • 25% off

    21 Dec 2018 - 28 Dec 2018

    £926.12 £694.50

  • 20% off

    28 Dec 2018 - 4 Jan 2019

    £926.12 £740.80

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