Dorset Retreats for 4 People

Give yourself and your family some TLC and book a break in a holiday cottage for 4 in Dorset. Explore this beautiful county by day and return to your own private retreat. A Dorset getaway is good for the heart and soul, and offers a great opportunity for everyone to catch up and spend quality time together.Read more

Summer getaway with long days on the beach, or winter retreat with toasty open fires and sofas perfect snuggling. Modern conversion with bubbling hot tub, or quaint cottage nestled in the heart of beautiful countryside. Wherever and however you envisage your getaway with your friends and family, let Classic Cottages help you create your dream holiday. Dorset is a county begging to be explored, so browse our list of 35 available cottages for 4 and let your Dorset faucet flow.

Dorset Getaways for 4

From country to coast, Dorset offers as much opportunity for relaxation as exploration. Gather your loved ones and dive straight in.

At Classic Cottages we pride ourselves on marketing the highest quality self catering cottages in Dorset. All are regularly inspected and are totally equipped with everything you could need and more during your stay. We will guide you through every step of the way, from start to finish. The only thing you need to think about? Kicking back and enjoying your holiday.

35 luxury self catering cottages that sleep 4 people in Dorset

New bookings can be placed for any holiday arriving on or after the 1st March 2021. COVID-19

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £359

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 £359

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

7 nights from £389

Old Sandpitts Cottage

4504

2 bedroom thatched self catering cottage near Bridport, Dorset.


Tucked away down its own private track, this picture-perfect thatched cottage is a little gem. Surrounded by its own private garden, the cottage is very peaceful and offers space f...

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

7 nights from £389

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

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £409

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 £409

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £414

Cedar Lodge

4014

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


Cedar Lodge is a cosy cottage in a quiet rural location. All on one level, the open plan living-room with kitchen and dining areas create a very sociable space for a couple or smal...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £414

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

7 nights from £415

Celtic Blessing

2256

2 bedroom holiday cottage near Bridport, Dorset.


Close to Dorset's spectacular Jurassic Coast, the popular market town of Bridport and the harbour and beach at West Bay, this cottage has stunning views of the gentle Dorset countr...

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

7 nights from £415

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £424

The Old Coach House

1386

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


This pretty, detached former coach house is in beautiful rural Dorset, and within easy reach of the stunning World Heritage Jurassic coastline. The Old Coach House has a spaciou...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £424

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £449

Ivy Cottage

4122

2 bedroom, dog friendly holiday cottage in Cattistock near Dorchester, Dorset.


Imagine life in a tranquil Dorset village and Ivy Cottage is just the sort of place you may picture in your mind. Set in the midst of an Area of Outstanding Natural Beauty, the cot...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £449

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

7 nights from £463

September Cottage

2948

2 bedroom self catering cottage near the sea near Weymouth, Dorset.


This comfortable semi-detached family home is on the edge of the countryside, yet only three miles from Weymouth with its sandy beaches and historic quay. A 20 minute walk takes yo...

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

7 nights from £463

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

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

7 nights from £496 *

Sturthill Stable

2829

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


This beautiful barn conversion at the heart of a working dairy farm is just inland from Dorset's spectacular Jurassic Coast and its beaches. The rural setting will please all the f...

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

7 nights from £496 *

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

7 nights from £510

Dairyman’s Cottage

2094

2 bedroom, rural holiday cottage near Shaftesbury, Dorset.


Located in an Area of Outstanding Natural Beauty, Hatts Farm is a working farm set in 150 acres on the Dorset and Wiltshire border. Dairyman's Cottage is traditional yet contempora...

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

7 nights from £510

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