Dorset Cottages Sleeping Two People

Head to Dorset for Hardy-esque holidays and write your own love story in a holiday cottage sleeping two people. Be it a solo getaway, romantic retreat or catch up with a family member or friend, our cottages provide an idyllic base in Dorset. Take a step closer to a dream holiday and secure your favourite cottage. All of our properties are handpicked and personally inspected. Read more

Although providing the perfect bolthole, days out for a pair are readily available from your Dorset cottage’s doorstep. A romantic break for two is just the ticket.

The region is imbued with romantic ruins and icons of the region’s mythological past – perfect for investigating with a friend or partner. Take a look at castles such as Lulworth, or the majestic Sherbourne Abbey.  Or step even further back in time: climb up the Iron Age hill-forts overlooking the River Stour or explore sites associated with Celtic mythology such as Badbury Rings, Maiden Castle, Knowlton Circles and the Cerne Giant.

It’s not only the man-made architecture which is revered in the county: the iconic Old Harry Rocks and the impressive Durdle Door are equally as stunning. Pack a picnic full of local produce and head along the coastal path to best appreciate these natural wonders. 

For more seaside adventures for two, Hengitsbury Head is the ideal spot for a sunset stroll. Chat with fishermen reeling in the day’s catch, then climb the hill to receiving stunning panoramic views. Although you won’t want to try Chesil Beach’s full 18-mile length, stroll along this impressive spit for a different perspective on the Portland coast. Then head to Wyke Regis to soak up the village’s relaxed ambience or gorge on oysters and the freshest fish with a cooling white wine at one of its famed coastal restaurants. For added luxury on your seaside break, why not choose a holiday cottage with a hot tub for extra relaxation while away.

Dorset’s literary son, Thomas Hardy, used the county as a back-drop for many of his novels, so inspiriting to him were its hills, rivers and towns. Pull on your hiking boots and explore the Blackmoor Vale, north of Hardy’s home town – the pretty Dorchester. Hardy waxes lyrical on the area, stating that, “Here in the valley, the world seems to be constructed upon a smaller and more delicate scale…The atmosphere below is languorous…and the horizon beyond is of deepest ultramarine.' With recommendations such as this, how could you not be intrigued?

Pick from 40 Dorset retreats sleeping two

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £442

2 bedroom, rural cottage near the beach near Bridport, Dorset.


The Parlour is an excellent choice for a family, with French windows opening out onto an enclosed gravelled patio, comfortable accommodation for five guests – one of the three sing...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £442

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £488

2 bedroom, rural holiday cottage near Shaftesbury, Dorset.


Semi-detached Hatts Barn is a contemporary, reversed level barn conversion on a wide south-facing terrace. The large en suite master bedroom and a twin bedded family room (the beds...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £488

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £493

3 bedroom self catering cottage in Wareham, Dorset.


Wareham is the gateway to the Jurassic Coast, a fabulous base from which to explore the Isle of Purbeck. Just within the ancient Saxon walls of this historic market town, Northgate...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £493

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

7 nights from £546

3 bedroom, dog friendly cottage near Wimborne Minster, Dorset.


This is an excellent base for exploring rural and coastal Dorset. Cranborne Chase (an Area of Outstanding Natural Beauty) is on the doorstep, and the beaches of the Jurassic Coast ...

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

7 nights from £546

  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £558

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


Barn Owls Cottage, a semi-detached cottage converted from an 18th Century stone barn, has retained much of its original character with inset fossils and huge oak beams. The kitchen...

  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £558

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

7 nights from £561

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 £561

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

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £592

3 bedroom thatched, dog friendly cottage in Tolpuddle, Dorset.


This very pretty thatched cottage is in the tranquil historic village of Tolpuddle, surrounded by beautiful countryside and just 15 miles from the World Heritage Jurassic Coast. Wi...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £592

  • Sleeps 6
  • Dogs welcome
  • Changeover Fri

7 nights from £606

3 bedroom, dog friendly holiday cottage near Lyme Regis, Dorset.


Imagine spending a week in a fabulous former dairyman’s cottage with all mod-cons! This very stylishly furnished, yet quirky, semi-detached cottage is in the village of Morcombelak...

  • Sleeps 6
  • Dogs welcome
  • Changeover Fri

7 nights from £606

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

7 nights from £618

3 bedroom holiday cottage in Corfe Castle, Dorset.


You will be completely spoilt for choice in this stunning part of Dorset – along the Jurassic Coast and within very easy reach are Lulworth Cove and Durdle Door with their famous c...

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

7 nights from £618

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

7 nights from £659

4 bedroom holiday cottage near the beach in Studland, Dorset.


The Isle of Purbeck is a stunning Area of Outstanding Natural Beauty between Poole and Swanage boasting one of the most spectacular coastlines in Dorset. Sunnyholme, an extremel...

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

7 nights from £659

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