Two night breaks in Dorset

A weekend away or two night short break in Dorset is so simple. No major preparations or need to pack up your life, just the perfect excuse to get away from it all for your favourite holiday cottage and slip under the radar of everyday life. With hand picked cottages across the south and west of the country there are endless places to escape to for a two night break with Classic Cottages. Take a look and see...

We have 29 holiday cottages available in Dorset for a two night break

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

7 nights from £337

The Stables

1965

1 bedroom, rural holiday cottage near Dorchester, Dorset.


Dorset’s World Heritage Jurassic Coast is close to this comfortably furnished, single-storey, spacious cottage. Set within the grounds of the owner’s home, The Stables is self-cont...

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

7 nights from £337

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

7 nights from £345

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 £345

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

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

7 nights from £345

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 £345

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £348

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 £348

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £399

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 £399

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

7 nights from £446 *

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 £446 *

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

7 nights from £446 *

Gamekeeper's Cottage

4523

2 bedroom self catering cottage near Dorchester, Dorset.


Second in a row of pretty terraced cottages, this stylish property has been newly renovated to a very high standard. Gamekeeper's Cottage is one of four at Dominey's Yard, nestled ...

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

7 nights from £446 *

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

7 nights from £446 *

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 £446 *

Our guests rate us 4.8/5 on Feefo, the independent review site.

  • 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

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £407

Wayside Cottage

4484

2 bedroom thatched, dog friendly cottage near Beaminster, Dorset.


A gorgeous, chocolate-box cottage that is the ideal escape, nestled in the heart of one of Dorset's picturesque villages. Just a stone's throw from the lovely local pub, Wayside Co...

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £407

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