October Breaks in Dorset

Great weather often hangs around until well into October in Dorset, so to celebrate the final flourishes of summer properly why not book a luxury self-catering cottage? Snugly one-bed retreat in a charming town, romantic hideaway with amazing sea views, or cottage in the country with space for all the gang, we'll help you pave the way to the holiday of your dreams this October. 

For a truly romantic getaway, browse through our list of cottages with hot tubs available this October. Spend your days exploring and soaking in the last of the summer rays, and then when you've had your fill return to your home-from-home and hop into a bubbling hot tub. Or how about a family-friendly cottage, perfect for little kids and big kids alike? October is a great time of year for families to make the most of all that Dorset has to offer with half term around the corner and lots of spook-tacular celebrations taking place ahead of Halloween. If you would like to revel in some peace and quiet, we have plenty of secluded cottages, offering lots of privacy and plenty of space for some quality R&R. At Classic Cottages, we pride ourselves on marketing the finest self-catering cottages around, handpicking and personally inspecting each one. Find your favourite today. 

Pick from 31 cottages in Dorset this October

Dog friendly safari tent glamping for six persons near Shaftesbury, Dorset.


Glamping at Black Pig Retreats allows you to escape the everyday; park your car, load your luggage onto the farm's all-terrain vehicle and your countryside adventure begins, canvas...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £587 - £810

Dog friendly safari tent glamping for six near Shaftesbury, Dorset.


Glamping at Black Pig Retreats allows you to escape the everyday and enjoy a fabulous holiday with a difference, where you can cook with fire, collect logs, listen to birdsong and ...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £587 - £810

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

Price per week £624 - £876

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

Price per week £630 - £806

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

Price per week £639 - £896

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

Price per week £649 - £910

We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.

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

Price per week £762 - £974

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

Price per week £1037 - £1895 *

* Includes 30% off for parties up to 8 + 2 cots between 1 Sep and 15 Dec 2018. Bedroom 1 and the single bed in Bedroom 3 are excluded at this rate

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


This beautiful stone farmhouse has something very special indeed – it comes with a 450 acre wildlife and nature reserve and a unique relationship with Dorset Wildlife Trust. Quite ...

  • Sleeps 9 + 2 cots
  • Dogs welcome
  • Changeover Fri

Price per week £730 - £1023


This working farm on the edge of the historic village of Chideock stretches gently downhill to the Jurassic Coast where one of Dorset's most famous landmarks – Golden Cap – rises a...

  • Sleeps 9 + 3 cots in 3 properties
  • Changeover Sat

Price per week £1131 - £1421

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