Dorset Retreats for 4 People

Dorset Retreats for 4 People

Give yourself and your family some TLC and book a break in a holiday cottage for 4 in Dorset. Explore this beautiful county by day and return to your own private retreat. A Dorset getaway is good for the heart and soul, and offers a great opportunity for everyone to catch up and spend quality time together.Read more

Summer getaway with long days on the beach, or winter retreat with toasty open fires and sofas perfect snuggling. Modern conversion with bubbling hot tub, or quaint cottage nestled in the heart of beautiful countryside. Wherever and however you envisage your getaway with your friends and family, let Classic Cottages help you create your dream holiday. Dorset is a county begging to be explored, so browse our list of 43 available cottages for 4 and let your Dorset faucet flow.

Dorset Getaways for 4

From country to coast, Dorset offers as much opportunity for relaxation as exploration. Gather your loved ones and dive straight in.

At Classic Cottages we pride ourselves on marketing the highest quality self catering cottages in Dorset. All are regularly inspected and are totally equipped with everything you could need and more during your stay. We will guide you through every step of the way, from start to finish. The only thing you need to think about? Kicking back and enjoying your holiday.

43 luxury self catering cottages that sleep 4 people in Dorset

The Old School Gables is a 2 bedroom cottage near the market town of Bridport, Dorset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £439

The Old School Gables

2490

2 bedroom cottage near the market town of Bridport, Dorset.


The pretty Dorset village of Drimpton is set in lovely countryside, a short drive inland from the stunning Jurassic Coast. This original school house has been converted into extrem...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £439

The Gardens is a 2 bedroom, dog friendly self catering cottage in Sherborne, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £453

The Gardens

5406

2 bedroom, dog friendly self catering cottage in Sherborne, Dorset.


From the rolling hills of the Dorset countryside to the beautiful historic streets of Sherborne and down to the Jurassic Coast, explore it all whilst staying at The Gardens. This c...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £453

Old Sandpitts Cottage is a 2 bedroom thatched cottage near Bridport, Dorset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £459

Old Sandpitts Cottage

4504

2 bedroom thatched cottage near Bridport, Dorset.


Tucked away down its own private track, this picture-perfect thatched cottage is a little gem. Surrounded by its own private garden, the cottage is very peaceful and offers space f...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £459

Beehive Cottage is a 2 bedroom thatched, dog friendly cottage near Dorchester, Dorset.
  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £474

Beehive Cottage

4073

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


Beehive Cottage is a charming and cosy cottage, on a quiet lane opposite St Mary's church in the village of Puddletown. Surrounded by farmland, the pretty village is nestled in the...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £474

The Old Coach House is a 2 bedroom, dog friendly cottage near the county town of Dorchester, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £491

The Old Coach House

1386

2 bedroom, dog friendly cottage near the county town of Dorchester, Dorset.


This pretty detached former coach house can be found in the rural Dorset countryside, within easy reach of the stunning coastlines of the Jurassic Coast, a World Heritage Site. ...

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

7 nights from £491

Pippins is a 3 bedroom, dog friendly holiday cottage near Beaminster, Somerset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £498

Pippins

5360

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


Pippins is a picture postcard country cottage nestled in the charming Somerset village of North Perrott - not far from the Dorset border. This cosy home can cater for all of the fa...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £498

Ivy Cottage is a 2 bedroom, dog friendly cottage in Cattistock near Dorchester, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £519

Ivy Cottage

4122

2 bedroom, dog friendly 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 (now ren...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £519

Celtic Blessing is a 2 bedroom cottage near Bridport, Dorset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £519

Celtic Blessing

2256

2 bedroom 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
  • No pets
  • Changeover Fri

7 nights from £519

Choose from our exclusive collection at the best prices with real time availability.

Tolpuddle Cottage is a 3 bedroom thatched, dog friendly cottage in Tolpuddle, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £542

Tolpuddle Cottage

3752

3 bedroom thatched, dog friendly cottage in Tolpuddle, Dorset.


This pretty thatched cottage is in the tranquil historic village of Tolpuddle, just 15 miles from the World Heritage Jurassic Coast. An ideal base for a family holiday or perfect f...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £542

The Old Dairy is a 2 bedroom, dog friendly former milking parlour near Blandford Forum, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £548

The Old Dairy

4740

2 bedroom, dog friendly former milking parlour near Blandford Forum, Dorset.


This former milking parlour that served the local farm has been beautifully converted into a fabulous holiday home. Situated in a picturesque Dorset village that is full of charact...

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

7 nights from £548

Woodcutter's Cottage is a 2 bedroom cottage with outside pool near Dorchester, Dorset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £566

Woodcutter's Cottage

4524

2 bedroom cottage with outside pool near Dorchester, Dorset.


Rolling hills, bustling market towns, rich history and stunning beaches - have we persuaded you to holiday in Dorset yet? Finding a lovely cottage to stay in is the only thing you ...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £566

Gamekeeper's Cottage is a 2 bedroom cottage with outside pool near Dorchester, Dorset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £566

Gamekeeper's Cottage

4523

2 bedroom cottage with outside pool near Dorchester, Dorset.


Second in a row of pretty terraced cottages, this stylish property has been newly renovated to a very high standard. Gamekeeper's Cottage is one of four at Dominey's Yard, nestled ...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £566

Poacher's Cottage is a 2 bedroom cottage with outside pool near Dorchester, Dorset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £566

Poacher's Cottage

4522

2 bedroom cottage with outside pool near Dorchester, Dorset.


Tucked away in the picturesque village of Buckland Newton, Poacher's Cottage is one of four gorgeous properties making up Dominey's Yard. Situated perfectly for exploring the beaut...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £566

Dairyman’s Cottage is a 2 bedroom, rural holiday cottage near Shaftesbury, Dorset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £600

Dairyman’s Cottage

2094

2 bedroom, rural holiday cottage near Shaftesbury, Dorset.


Located in an Area of Outstanding Natural Beauty, Hatts Farm is a working farm set in 150 acres on the picturesque Dorset and Wiltshire border. Dairyman's Cottage is a traditio...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £600

We’re here to help you find your perfect place to stay 7 days a week.

Rectory Cottage is a 2 bedroom cottage near Bridport, Dorset
  • Sleeps 4 + cot
  • No pets
  • Changeover Mon

7 nights from £627

Rectory Cottage

4795

2 bedroom cottage near Bridport, Dorset


Hidden away in the grounds of a Grade II Listed former rectory, this picture-perfect cottage is a delightful Dorset escape. From the moment you pull into the driveway you will love...

  • Sleeps 4 + cot
  • No pets
  • Changeover Mon

7 nights from £627

Barbridge Cottage is a 2 bedroom, rural holiday cottage near Bridport, Dorset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £653

Barbridge Cottage

1805

2 bedroom, rural holiday cottage near Bridport, Dorset.


With beaches, fossil hunting, walks and lovely pubs all around, Barbridge Cottage is the ideal home-away-from-home to explore West Dorset and the Jurassic Coast. Up a short, unm...

  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £653

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 £653 *

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 £653 *

Woodville Cottage is a 3 bedroom, dog friendly home near the beach in Lyme Regis.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Wed

7 nights from £725

Woodville Cottage

5151

3 bedroom, dog friendly home near the beach in Lyme Regis.


Woodville Cottage is a pretty and charming property, an annexe to a Grade II Listed Georgian building. Hidden away from the hustle and bustle of the elegant seaside town of Lyme Re...

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

7 nights from £725

Halcyon Cottage is a 2 bedroom cottage near the beach and Lulworth Cove near Dorchester, Dorset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £730

Halcyon Cottage

4693

2 bedroom cottage near the beach and Lulworth Cove near Dorchester, Dorset.


Less than two miles from Lulworth Cove, part of the only World Heritage Site in England, Halcyon Cottage is a pretty, detached stone cottage in the heart of the village of West Lul...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £730

The Old Dairy is a 2 bedroom, dog friendly cottage near Wimborne Minster, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £756

The Old Dairy

5551

2 bedroom, dog friendly cottage near Wimborne Minster, Dorset.


Situated within the southern neolithic ring of Knowlton Church and Earthworks and perfectly positioned under a Dark Sky Reserve, is The Old Dairy; a stylish and modern conversion t...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £756

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Seymour Barn is a 2 bedroom, dog friendly self catering cottage in Bridport, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £815

Seymour Barn

5314

2 bedroom, dog friendly self catering cottage in Bridport, Dorset.


With the bustling market town of Bridport within striking distance, this beautiful barn conversion is the perfect home-away-from-home. A delightful spot to explore all the beauty a...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £815

The Old Mill is a 2 bedroom, unique, dog friendly converted mill near Dorchester, Dorset.
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £871

The Old Mill

4503

2 bedroom, unique, dog friendly converted mill near Dorchester, Dorset.


If you are looking for a beautifully unique and special property for a perfect Dorset holiday then look no further than The Old Mill. Formerly a working mill, this gorgeous propert...

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

7 nights from £871

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

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 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
  • 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

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

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 £606

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 £606

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

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

Sunnyholme is a 4 bedroom house near the beach in Studland, Dorset.
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £805

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
  • No pets
  • Changeover Fri

7 nights from £805

We’ve been raising the standards of self catering holidays since 1977.

Sandy Days is a 3 bedroom, dog friendly cottage near the beach in Christchurch.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £898

Sandy Days

3215

3 bedroom, dog friendly cottage near the beach in Christchurch.


Avon beach, Christchurch Harbour, the New Forest National Park and the Jurassic Coast are all nearby to this recently renovated holiday bolthole. The cool shades of blue and the pl...

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

7 nights from £898

Gardener's Cottage is a 3 bedroom cottage with outside pool near Dorchester, Dorset.
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £942

Gardener's Cottage

4525

3 bedroom cottage with outside pool near Dorchester, Dorset.


A stay at Gardener's Cottage brings you everything you could wish for in a holiday location - spacious rooms, beautiful furnishings and a stunning setting complete with outdoor hea...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £942

Acorns is a 3 bedroom cottage in Corfe Castle, Dorset.
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £983

Acorns

4828

3 bedroom cottage in Corfe Castle, Dorset.


Set on a private, secluded plot, Acorns is a wonderful family holiday home. Recently renovated to a very high standard, this detached house in the historic village of Corfe Castle ...

  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £983

Cobb Cottage is a 4 bedroom, dog friendly cottage with sea views in Lyme Regis, Dorset.
  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1133

Cobb Cottage

3243

4 bedroom, dog friendly cottage with sea views in Lyme Regis, Dorset.


Escape to the coast and this fabulous cottage where you can watch the seascape change all day long. Just minutes from the harbour at Lyme Regis and its iconic Cobb, this Grade I...

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1133

Beech Cottage is a 5 bedroom, dog friendly cottage with views over the nature reserve near Bridport, Dorset.
  • Sleeps 9 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1080

Beech Cottage

2887

5 bedroom, dog friendly cottage with views over the nature reserve near Bridport, Dorset.


This beautiful stone farmhouse has something very special indeed - it comes with a 450 acre nature reserve and a unique relationship with Dorset Wildlife Trust, offering comfortabl...

  • Sleeps 9 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1080

The Old Manor House is a 5 bedroom, dog friendly cottage near the beach near Lyme Regis.
  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1645

The Old Manor House

4124

5 bedroom, dog friendly cottage near the beach near Lyme Regis.


Less than half a mile from the World Heritage Jurassic Coast, The Old Manor House is a beautiful 16th Century, Grade II Listed house, full of character with a delightful enclosed g...

  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1645

We are Gold accredited with the Green Tourism Business Scheme.

Buddlewall is a 6 bedroom thatched, dog friendly home near Lyme Regis, South Devon.
  • Sleeps 12 + 2 cots
  • Dogs welcome
  • Changeover Thu

7 nights from £1608

Buddlewall

3979

6 bedroom thatched, dog friendly home near Lyme Regis, South Devon.


Buddlewall is an historic east Devon farmhouse, in a beautiful hidden rural setting, a short drive inland from the spectacular World Heritage east Devon and Dorset Jurassic Coast. ...

  • Sleeps 12 + 2 cots
  • Dogs welcome
  • Changeover Thu

7 nights from £1608

West Hembury Farm

  • Sleeps 8 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £1089

Hatts Farm

  • Sleeps 9 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £1215

Doghouse Farm

  • Sleeps 9 + 3 cots in 3 properties
  • Changeover Sat

7 nights from £1293

Dominey's Yard

  • Sleeps 18 + 4 cots in 4 properties
  • Changeover Fri

7 nights from £2641