Holiday Cottages Sleeping 5 People in Dorset

Bundle up your favourite people and get on your way to Dorset. We have a selection of 20 self-catering cottages sleeping up to 5 people available. Invite four of your friends or family, or simply make use of the extra space, our cottages that sleep 5 combine home-comforts with modern luxuries. Don't miss out on your favourite and book your luxury self-catering cottage now. Read more

Take a winter break in a rural retreat to put a fun twist on traditional celebrations, and then get planning for summer and enjoy a quintessential seaside holiday. Whether you choose a short break or a whole month of exploration and relaxation, Dorset provides an idyllic playground. From its stunning Jurassic coastline to its beautiful rolling countryside to its pretty medley of towns and villages, take your pick of activities for the day and then return to your own private accommodation.

If you have got friends who you haven't seen for a while or are looking for an excuse to get the family together for some quality time, our self-catering cottages sleeping 5 people offer ample space and comfort. With real beds for everyone to snuggle into, we make sure everything you could need and more is available and no one gets cut short without a mug to drink from or somewhere comfy to settle into. You'll even find there are enough teaspoons for everyone. 

Dorset Cottages that Sleep 5 People 

At Classic Cottages we want your holiday experience to be the best it can be for you and everyone in your party. That's why all of our cottages are handpicked; personally inspected and fully equipped for your total ease and comfort. We are always on hand to offer support, and will help you every step of the way towards the holiday of your dreams. Many of our cottages are dog-friendly too, meaning everyone can enjoy a holiday in Dorset.

 

Find your favourite Dorset cottage for 5 from our 20 available retreats

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

7 nights from £458

Meadowbank

2644

3 bedroom house with countryside views near Bridport, Dorset.


If you are looking for a peaceful, rural setting to spend your well deserved holiday, then look no further. This sunny south-facing cottage is sat perfectly on the edge of the beau...

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

7 nights from £458

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

7 nights from £490

The Parlour

2662

2 bedroom cottage with views of Golden Cap near Bridport, Dorset


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

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

7 nights from £490

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

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

7 nights from £585

Hatts Barn

2093

2 bedroom, rural holiday cottage near Shaftesbury, Dorset.


Hatts Farm is a working farm located in an Area of Outstanding Natural Beauty. The farm spreads over 150 acres, located in the stunning countryside of the Dorset and Wiltshire bord...

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

7 nights from £585

  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £688

Park Farm Byre

4956

3 bedroom, dog friendly holiday cottage with hot tub near Dorchester, Dorset.


Tucked away in a rural location, you will find Park Farm Byre, a stylish retreat complete with wood-fired hot tub. All on one level (apart from two steps from the sitting-room to t...

  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £688

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

7 nights from £600

Crosskeys Cottage

4855

3 bedroom, dog friendly holiday cottage near Beaminster, Dorset.


Situated in the pretty west Dorset village of Broadwindsor, surrounded by countryside and not far from the coast, Crosskeys Cottage is a wonderful place to spend your holiday. Buil...

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

7 nights from £600

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

7 nights from £607

Sturthill Stable

2829

3 bedroom, dog friendly barn conversion set within a working farm 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 £607

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

7 nights from £614

Bay Tree Cottage

4835

3 bedroom, dog friendly cottage near Bridport, Dorset.


Situated in a sleepy west Dorset village, just a short drive from the spectacular Jurassic Coast, you will find this pretty terraced cottage. Recently renovated, Bay Tree Cottage o...

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

7 nights from £614

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £619

Barn Owls Cottage

3015

3 bedroom, dog friendly cottage near Bridport, Dorset.


Barn Owls Cottage is a semi-detached cottage that has been converted from an 18th Century stone barn. Despite having stylish modern fittings, it has still retained much of its orig...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £619

We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.

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

7 nights from £678

2 Penny’s Cottages

2531

3 bedroom house in the historic village of Corfe Castle, Dorset.


Set in the historic village of Corfe Castle, 2 Penny's Cottages is a semi-detached family house that welcomes all its visitors, it is a real home-from-home. The property has been b...

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

7 nights from £678

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

7 nights from £723

Sunnyholme

1460

4 bedroom house 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 is an extrem...

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

7 nights from £723

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