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 44 available cottages and secure your September retreat today.

We have 44 Dorset cottages available in September

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

7 nights from £429

The Stables

1965

1 bedroom, rural holiday cottage near the county town of Dorchester, Dorset.


This quaint cottage is set within the rural hamlet of Pallington. The Stables is a self-contained, single storey cottage with a welcoming open plan design. The entrance hall leads ...

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

7 nights from £429

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

7 nights from £449

The Linhay

2661

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 £449

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

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

7 nights from £449

The Dairy

2663

1 bedroom cottage near the Jurassic Coast near Bridport, Dorset.


The Dairy is another extremely comfortable single-storey cottage in this small and friendly farm development. This property has French doors to its own enclosed outside space – the...

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

7 nights from £449

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £453

Swallows' Rest

4644

1 bedroom, dog friendly cottage near Beaminster, Dorset.


The sleepy west Dorset countryside awaits you at this cute bolthole for two (plus your four-legged friends). Tucked away at the end of the owners' garden, this converted barn is hi...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £453

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

7 nights from £453

Owl's Nest Cottage

2942

1 bedroom, dog friendly 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 £453

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £466

Badgers Cottage

3014

1 bedroom, dog friendly cottage near Bridport, Dorset.


This pretty semi-detached cottage for two is nestled within an Area of Outstanding Natural Beauty on West Hembury Farm. Badgers Cottage is an 18th Century stone barn that has be...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £466

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £513

Pound Farm Cottage

4076

1 bedroom thatched cottage near Sherborne, Dorset.


Pound Farm Cottage is a hidden gem; this listed thatched cottage has been thoughtfully renovated to create a spacious, stylish holiday home, retaining many of the original features...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £513

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  • 15% off

    21 Jan 2022 - 26 Jan 2022

    £361.60 £307.36

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

7 nights from £590

Toby's Hut

4723

1 bedroom, dog friendly shepherds hut near Lyme Regis, Dorset.


Located in the west Dorset Area of Outstanding Natural Beauty and just a 15 minute drive from fabulous Lyme Regis, Toby's Hut is a bespoke Shepherd's Hut, sitting in a perfect spot...

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

7 nights from £590

Our property managers are local experts who handpick perfect places to stay.

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £635

The Chalet on the Beach

3351

Chalet on the beach sleeping two in Lyme Regis, Dorset.


Imagine a holiday right on the seashore of a very special beach, relaxing on your veranda with a glass of something refreshing, watching the gentle waves at one of the most famous ...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £635

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

7 nights from £745

La Cabine Francaise

4726

1 bedroom, dog friendly Shepherds Hut near Dorchester, Dorset.


Welcome to La Cabine Francaise, a glorious expanse of glamping bliss with a French twist. Set in the stunning Dorset countryside, this exclusive spot for two provides the perfect r...

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

7 nights from £745

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