Holiday Cottages Sleeping 5 People in Dorset

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

The Parlour is a 2 bedroom cottage with views of Golden Cap near Bridport, Dorset
  • Sleeps 5 + cot
  • No pets
  • Changeover Sat

7 nights from £546

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
  • No pets
  • Changeover Sat

7 nights from £546

Quince Cottage is a 3 bedroom, dog friendly cottage close to the beach near Bridport, Dorset.
  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £598

Quince Cottage

5190

3 bedroom, dog friendly cottage close to the beach near Bridport, Dorset.


With the World Heritage Jurassic Coast within one mile's walk, Quince Cottage is a welcoming home in the pretty West Dorset village of Chideock. This charming home is the perfect l...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £598

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

Hatts Barn is a 2 bedroom, rural holiday cottage near Shaftesbury, Dorset.
  • Sleeps 5 + cot
  • No pets
  • Changeover Fri

7 nights from £615

Hatts Barn

2093

2 bedroom, rural holiday cottage near Shaftesbury, Dorset.


Hatts Farm is a working farm located in a National Landscape. The farm spreads over 150 acres, located in the stunning countryside of the Dorset and Wiltshire border. Hatts Barn...

  • Sleeps 5 + cot
  • No pets
  • Changeover Fri

7 nights from £615

Park Farm Byre is a 3 bedroom, dog friendly holiday cottage near Dorchester, Dorset.
  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £740

Park Farm Byre

4956

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


Tucked away in a rural location, you will find Park Farm Byre, a stylish retreat complete with hot tub and perfectly situated on a number of country and woodland walks. All on one ...

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

7 nights from £740

Old Sandpitts Lodge is a 3 bedroom thatched self catering cottage near Bridport, Dorset.
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £573

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
  • No pets
  • Changeover Fri

7 nights from £573

Sturthill Stable is a 3 bedroom, dog friendly barn conversion set within a working farm near Bridport, Dorset.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £638

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 £638

Bay Tree Cottage is a 3 bedroom, dog friendly cottage near Bridport, Dorset.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £645

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. Bay Tree Cottage offers all the deligh...

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

7 nights from £645

Barn Owls Cottage is a 3 bedroom, dog friendly cottage near Bridport, Dorset.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £690

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 £690

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

2 Penny’s Cottages is a 3 bedroom house in the historic village of Corfe Castle, Dorset.
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £723

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
  • No pets
  • Changeover Sat

7 nights from £723

St Peter's Cottage is a 3 bedroom thatched, dog friendly cottage near Dorchester, Dorset.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £726

St Peter's Cottage

5135

3 bedroom thatched, dog friendly cottage near Dorchester, Dorset.


Dating back to the early 17th Century, this picture perfect, Grade II Listed thatched cottage sits in the heart of a rural Dorset village. Recently renovated by the owners, St Pete...

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

7 nights from £726

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