Dorset Cottages Available in 2020

Plan a year to remember and book your perfect holiday cottage in Dorset. All of our luxury self-catering cottages are handpicked onto our books and are fully equipped, ensuring your holiday is the best it can be. Read more

 Now's a great time to be booking for next year. Our portfolio gets better year after year, with all the old favourites and some stunning new additions, so get in there quick and book your 2020 holiday cottage before someone else does. Browse our list of 32 available cottages..

 

Pay only £30 today and the remainder of your deposit is not due until 5th September, giving you all summer to sit back and relax, knowing that extra special place is all yours for 2020*. From Cornwall to Dorset, Devon to Somerset and even as far as the Isle of Wight, take a look at our collection now and start dreaming of your next holiday with Classic Cottages.

 

Pick a place close to the coast for that year-round holiday vibe, or book a holiday townhouse to be close to every convenience. Escape to the country for peace and quiet or take to the moors for walks through wide open spaces, we’ve got 32 holiday cottages for 2020 you to choose from...

 

*Click here for terms and conditions.

 

 

32 cottages available in Dorset for 2020

  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £323

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


This cosy, compact, delightful bolthole for two is set in a wonderfully tranquil hamlet in north Dorset with village shops and a choice of two pubs within two miles. Built in lo...

  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £323

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

7 nights from £325

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 windows to its own enclosed outside space – t...

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

7 nights from £325

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

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

7 nights from £330

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 £330

View
  • 30% off

    2 Aug 2019 - 9 Aug 2019

    £725.00 £507.50

  • 20% off

    23 Aug 2019 - 30 Aug 2019

    £725.00 £580.00

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £338

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


Badgers Cottage, a snug semi-detached cottage for two, is set in a farmyard, beautifully converted from an 18th Century stone barn. All on one level, the open plan design gives a w...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £338

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £365

1 bedroom, rural holiday cottage near Beaminster, Dorset.


Lottie’s Loft is a luxurious first floor barn conversion, a gorgeous bolthole surrounded by beautiful Dorset countryside. Exterior steps lead from the decking to a balcony with bes...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £365

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £453

Beach Chalet on the beach sleeping two in Lyme Regis, Dorset.


Imagine a holiday right on the seashore of a very special beach, relaxing on your veranda with a glass of something refreshing, watching the gentle waves at one of the most famous ...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £453

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

7 nights from £325

1 bedroom, dog friendly 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 3 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £325

View
  • 20% off

    3 Aug 2019 - 10 Aug 2019

    £592.00 £473.60

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £352

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 £352

Choose from our exclusive collection at the best prices with real time availability.

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £401

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


Beehive Cottage is a charming and cosy cottage for four, on a quiet lane opposite St Mary's church in the village of Puddletown. The village is surrounded by farmland, Thomas Hardy...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £401

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £406

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 creates a very sociable space for a couple or sma...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £406

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