Holiday cottages for 2021 in Dorset

Ready to start planning your 2021 adventure? Now's a great time to get ahead of the crowd. Snap up your 2021 holiday for just £30 this August and we will hold your reservation for you until the 1st October. Read more

Reserve your 2021 holiday for £30 - How it works

Choose your favourite cottage and preferred 2021 holiday dates and complete the reservation form. We will then email you with a reservation confirmation and invite you to take up our £30 reservation offer. All that's left to do is opt in via email and you're set! The full deposit will then be due on the 1 October 2020. And don't worry, there's no catch. This offer simply allows us to extend your reservation until 1 October for you. Please see our blog for further details.

Head to Cornwall, Devon, Somerset, Dorset, SussexIsle of Wight, Pembrokeshire or Kent with Classic in 2021. We have a portfolio of properties ready and waiting for you to start planning your next self catering holiday. Why not now and then relax later, knowing you've got your holiday for next year sorted. 

We have 36 Self catering holiday cottages for rent in 2021

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

7 nights from £758

2 bedroom, dog friendly self catering cottage in Dorchester, Dorset.


If you are looking for a beautifully unique and special property for a perfect Dorset holiday then look no further than The Old Mill. Formerly a working mill, this gorgeous propert...

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

7 nights from £758

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

7 nights from £389

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

7 nights from £395

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 £395

  • Sleeps 6
  • Dogs welcome
  • Changeover Sat

7 nights from £868

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


This beautiful, historical Grade II Listed semi-detached property oozes charm and luxury. Built in 1607, Oak House is one of the oldest houses in Yetminster and its dated enriched ...

  • Sleeps 6
  • Dogs welcome
  • Changeover Sat

7 nights from £868

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £495

3 bedroom thatched self catering cottage near Bridport, Dorset.


This very attractive thatched, detached property is in a tucked away rural setting in unspoilt west Dorset. Old Sandpitts Lodge is a very easy short drive inland from the fabulous ...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £495

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £569

3 bedroom self catering cottage near Yeovil, Dorset.


Meadows Barn is on the edge of the tranquil Dorset village of Halstock, with far reaching views over the surrounding countryside, ideal for a family holiday or a great base for fri...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £569

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £449

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
  • Dogs welcome
  • Changeover Fri

7 nights from £368 *

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 £368 *

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

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £394

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 £394

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £414

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

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