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. Read more

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 21 cottages in Dorset this October

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £355

Swallows' Rest

4644

1 bedroom, dog friendly holiday 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 £355

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

7 nights from £363

The Linhay

2661

1 bedroom 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 £363

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

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

7 nights from £363

The Dairy

2663

1 bedroom, rural cottage near the beach 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 £363

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £414

Pound Farm Cottage

4076

1 bedroom thatched self catering 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 £414

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

7 nights from £486 *

Poacher's Cottage

4522

2 bedroom self catering cottage near Dorchester, Dorset.


Tucked away in the picturesque village of Buckland Newton, Poacher's Cottage is one of four gorgeous properties making up Dominey's Yard. Situated perfectly for exploring the beaut...

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

7 nights from £486 *

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

7 nights from £486 *

Woodcutter's Cottage

4524

2 bedroom self catering cottage near Dorchester, Dorset.


Rolling hills, bustling market towns, rich history and stunning beaches - have we persuaded you to holiday in Dorset yet? Finding a lovely cottage to stay in is the only thing you ...

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

7 nights from £486 *

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £505

The Chalet on the Beach

3351

Cabin 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 £505

  • 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

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

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

7 nights from £745

La Cabine Francaise

4726

1 bedroom, dog friendly Shpeherds 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

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £390

The Old School Gables

2490

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 £390

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