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 October and we will hold your reservation for you until the 1st December. 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 December 2020. And don't worry, there's no catch. This offer simply allows us to extend your reservation until 1 December 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 book now and then relax later, knowing you've got your holiday for next year sorted. 

We have 38 Self catering holiday cottages for rent in 2021

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

7 nights from £758

The Old Mill

4503

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

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

7 nights from £395

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 £395

  • Sleeps 6
  • Dogs welcome
  • Changeover Sat

7 nights from £868

Oak House

4438

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 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £569

Meadows Barn

4293

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

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 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1680

The Old Manor House

4124

5 bedroom, dog friendly cottage near 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 £1680

  • 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

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  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £394

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 £394

  • Sleeps 12 + 2 cots
  • Dogs welcome
  • Changeover Thu

7 nights from £998 *

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 £998 *

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