Romantic Hideaways for Two in Dorset

Looking forward to spending some quality time with your partner away from the distractions of everyday life? Book a romantic break in Dorset, turn off your phone and give your beloved your undivided attention in your own private paradise. A romantic retreat will refresh your relationship and leave you with lots of happy memories.  Read more

Whether you are looking forward to starting off the New Year in style, taking a well-deserved summer break or fancy a cosy winter retreat together, the choices are endless for a romantic break together in Dorset. Browse through our selection of luxury self-catering cottages perfect for a couple's getaway. You may pick an old favourite or find a new place to be; whichever you choose you're guaranteed total comfort during your stay.

At Classic Cottages, we take quality accommodation seriously. Knowing the difference your accommodation can make to your experience, we pride ourselves on marketing only the finest self-catering cottages in Dorset. All of our cottages are handpicked; regularly checked and fully equipped, right down to the last teaspoon.

40 luxury cottages for couples in Dorset

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £394

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 £394

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

7 nights from £398

2 bedroom, rural holiday cottage near Shaftesbury, Dorset.


Dairyman’s Cottage is traditional yet contemporary, semi-detached and set on a south-facing terrace. The property has a welcoming feel, with a stunning open plan design downstairs,...

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

7 nights from £398

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

7 nights from £407

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


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

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

7 nights from £407

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

7 nights from £409

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 £409

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

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £431

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 £431

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £437

2 bedroom, rural self catering cottage near Beaminster, Dorset.


A stunning west Dorset location, amazing rural views and a truly luxurious property, Phoebes House is a hidden gem just a short drive inland from the famous Jurassic Coast. This de...

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £437

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

7 nights from £453

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 £453

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

7 nights from £529

2 bedroom, rural holiday cottage near Bridport, Dorset.


Nestling in a picturesque valley a fifteen minute drive from the Jurassic Coast, Barbridge Cottage is close to beaches, walks, fossil hunting, country houses, gardens and lovely pu...

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

7 nights from £529

  • Sleeps 7 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £671 *

4 bedroom, dog-friendly cottage with sea views near Bridport, Dorset.


Snuggled into the hillside with Golden Cap behind, The Guardhouse stands watch over this stunning part of the Jurassic Coast at Seatown, with sea views from the master bedroom and ...

  • Sleeps 7 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £671 *

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

7 nights from £419

3 bedroom holiday cottage near Bridport, Dorset.


This sunny south-facing cottage enjoys a quiet rural position on the edge of the beautiful village of Netherbury, a short drive from the beaches and cliffs of the World Heritage Ju...

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

7 nights from £419

Our property managers are local experts who handpick perfect places to stay.

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