Two night breaks in Dorset

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 UK, there are endless places to escape to for a two night break with Classic Cottages. Take a look and see...

Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.

We have 12 holiday cottages available in Dorset for a two night break

Loaf is a 1 bedroom, dog friendly self catering cottage near Bridport, Dorset.
  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

7 nights from £578

Loaf

6046

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


Loaf is a gorgeous and sympathetic restoration of an ancient Dorset granary with panoramic views across the Marshwood Vale. Its interiors are straight out of a magazine with design...

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

7 nights from £578

Bay Tree Cottage is a 3 bedroom, dog friendly cottage near Bridport, Dorset.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £556 *

Bay Tree Cottage

4835

3 bedroom, dog friendly cottage near Bridport, Dorset.


Situated in a sleepy west Dorset village, just a short drive from the spectacular Jurassic Coast, you will find this pretty terraced cottage. Bay Tree Cottage offers all the deligh...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £556 *

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  • 20% off

    17 Oct 2025 - 24 Oct 2025

    From £597.00 £477.60

Toby's Hut is a Luxury dog friendly shepherds hut with a hot tub near Lyme Regis, Dorset.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

From £90 per night

Toby's Hut

4723

Luxury dog friendly shepherds hut with a hot tub 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

From £90 per night

La Cabine Francaise is a 1 bedroom, dog friendly Shepherds Hut near Dorchester, Dorset.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Sat

From £75 per night

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

From £75 per night

Swallows' Rest is a 1 bedroom, dog friendly cottage near Beaminster, Dorset.
  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £393

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 £393

The Old Manor House is a 5 bedroom, dog friendly cottage close to the beach near Lyme Regis.
  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1619 *

The Old Manor House

4124

5 bedroom, dog friendly cottage close to the beach near Lyme Regis.


Less than half a mile from the World Heritage Jurassic Coast, The Old Manor House is a beautiful 16th Century, Grade II Listed house, full of character with a delightful enclosed g...

  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1619 *

Beehive Cottage is a 2 bedroom thatched, dog friendly cottage near Dorchester, Dorset.
  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £510 *

Beehive Cottage

4073

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


Beehive Cottage is a charming and cosy cottage, on a quiet lane opposite St Mary's church in the village of Puddletown. Surrounded by farmland, the pretty village is nestled in the...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £510 *

Buddlewall is a 6 bedroom thatched, dog friendly home near Lyme Regis, South Devon.
  • Sleeps 12 + 2 cots
  • Dogs welcome
  • Changeover Thu

7 nights from £1047 *

Buddlewall

3979

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 Thu

7 nights from £1047 *

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

Sandy Days is a 3 bedroom, dog friendly cottage near the beach in Christchurch.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £925

Sandy Days

3215

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 holiday bolthole. The cool shades of blue and the plantation shutters e...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £925

2 Penny’s Cottages is a 3 bedroom house in the historic village of Corfe Castle, Dorset.
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £760

2 Penny’s Cottages

2531

3 bedroom house in the historic village of Corfe Castle, Dorset.


Set in the historic village of Corfe Castle, 2 Penny's Cottages is a semi-detached family house that welcomes all its visitors, it is a real home-from-home. The property has been b...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £760

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