Holiday Cottages Sleeping 5 People in Dorset

Bundle up your favourite people and get on your way to Dorset. We have a selection of 22 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 22 available retreats

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

7 nights from £428

Meadowbank

2644

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 £428

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

7 nights from £465

The Parlour

2662

2 bedroom, rural cottage near the beach 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 £465

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

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

7 nights from £550

Hatts Barn

2093

2 bedroom, rural holiday cottage near Shaftesbury, Dorset.


Hatts Farm is a working farm set in 150 acres on the Dorset and Wiltshire border, located in an Area of Outstanding Natural Beauty. The semi-detached Hatts Barn is a contemporary, ...

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

7 nights from £550

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

7 nights from £488

Old Sandpitts Lodge

4377

3 bedroom thatched self catering cottage near Bridport, Dorset.


This very attractive thatched, detached property is in a tucked away rural setting in unspoilt west Dorset. Old Sandpitts Lodge is a very easy short drive inland from the fabulous ...

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

7 nights from £488

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

7 nights from £557

Old Down Cottage

1934

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 £557

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

7 nights from £558

Meadows Barn

4293

3 bedroom self catering cottage near Yeovil, 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 £558

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

7 nights from £573

Sturthill Stable

2829

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 £573

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £584

Barn Owls Cottage

3015

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 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £584

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  • Sleeps 6
  • Dogs welcome
  • Changeover Thu

7 nights from £618

Dairy Cottage

3192

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 Thu

7 nights from £618

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

7 nights from £631

2 Penny’s Cottages

2531

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 £631

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