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.

42 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
  • Dogs welcome
  • Changeover Fri

7 nights from £394

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 £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, and within easy reach of the stunning World Heritage Jurassic coastline. The Old Coach House has a spaciou...

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

7 nights from £407

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

  • 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

View
  • 10% off

    27 Sep 2019 - 4 Oct 2019

    £471.39 £424.25

  • 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 and neighbouring property Lottie's Loft (2565) both hidden gems just a short driv...

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

7 nights from £469 *

3 bedroom self catering cottage in rural 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 £469 *

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

7 nights from £471 *

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 £471 *

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

Loading more