Holiday Cottages in Dorset for June

We have handpicked 32 of the finest luxury cottages in Dorset available in June. All of our self catering cottages are personally inspected and fully equipped, so pack your bags and get ready for a well-deserved getaway. Times to truly relax are few and far between so seize the opportunity with both hands and enjoy all that Dorset has to offer.Read more

Dorset, a county packed full of stunning natural landscapes, famous geographical landmarks, country towns and postcard villages. Choose whether you'd like a secluded country retreat or cosy hub in a quaint town, and let your legs wander and your mind wonder. If you'd like to take the family away, we have plenty of big cottages available for you to choose from. If you'd like to stay in a dog-friendly retreat, browse our selection of dog-friendly cottages available in June. For romantic time together, why not pick a cottage with a hot tub?

Holiday Cottages in Dorset this June

However you envisage your Dorset getaway this June, we will help you find the holiday cottage of your dreams. All of our cottages are personally inspected and fully equipped to make sure only the highest standards are met. At Classic Cottages we understand the importance of quality accommodation and want your holiday to be as dreamy as possible. Because of this we make sure everything you need is provided and all else is taken care of, so all that's left for you to do? Relax. 

32 Dorset cottages available in June

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £447

1 bedroom, rural cottage near the beach near Bridport, Dorset.


The Linhay is a tucked away single-storey retreat – an ideal base for exploring the wonderful coastline. The cottage nestles alongside the barns, with a fully enclosed gravel court...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £447

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £458

1 bedroom, dog friendly self catering cottage near Bridport, Dorset.


Badgers Cottage, a snug semi-detached cottage for two, is set in a farmyard, beautifully converted from an 18th Century stone barn. All on one level, the open plan design gives a w...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £458

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  • 35% off

    15 Feb 2019 - 18 Feb 2019

    £238.00 £154.70

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

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £509

1 bedroom, rural holiday cottage near Beaminster, Dorset.


Lottie’s Loft is a luxurious first floor barn conversion, a gorgeous bolthole surrounded by beautiful Dorset countryside. Exterior steps lead from the decking to a balcony with bes...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £509

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £632

Beach Chalet on the beach sleeping two in Lyme Regis, Dorset.


Imagine a holiday right on the seashore of a very special beach, relaxing on your veranda with a glass of something refreshing, watching the gentle waves at one of the most famous ...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £632

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £500

2 bedroom dog friendly holiday cottage near 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 extreme...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £500

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £546

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 £546

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £546

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 £546

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £568

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 £568

We are Gold accredited with the Green Tourism Business Scheme.

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £583

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 £583

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £624

2 bedroom, dog friendly holiday cottage 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 £624

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

7 nights from £639

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


This pretty detached former coach house is in beautiful rural Dorset within easy reach of the stunning World Heritage Jurassic coastline. The Old Coach House has a spacious brig...

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

7 nights from £639

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £641

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 £641

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £685

2 bedroom, rural self catering cottage near Beaminster, Dorset.


A stunning west Dorset location, amazing rural views and a truly luxurious property, Phoebes House is a hidden gem just a short drive inland from the famous Jurassic Coast. This de...

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £685

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

7 nights from £581

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 £581

Our property managers are local experts who handpick perfect places to stay.

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

7 nights from £765

2 bedroom, rural holiday cottage near Shaftesbury, Dorset.


Semi-detached Hatts Barn is a contemporary, reversed level barn conversion on a wide south-facing terrace. The large en suite master bedroom and a twin bedded family room (the beds...

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

7 nights from £765

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

7 nights from £856

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 £856

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £857

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


This very pretty thatched cottage is in the tranquil historic village of Tolpuddle, surrounded by beautiful countryside and just 15 miles from the World Heritage Jurassic Coast. Wi...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £857

  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £875

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 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £875

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

7 nights from £880

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 £880

  • Sleeps 6
  • Dogs welcome
  • Changeover Fri

7 nights from £951

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 Fri

7 nights from £951

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.

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

7 nights from £1026

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 £1026

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

7 nights from £1030

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 £1030

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

7 nights from £1065

3 bedroom holiday cottage in Corfe Castle, Dorset.


Situated in the popular Dorset village of Corfe Castle, on the Studland peninsula, close to the coast, this Grade II Listed picture-book cottage enjoys views of the spectacular Nat...

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

7 nights from £1065

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

7 nights from £1098

4 bedroom holiday cottage 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, an extremel...

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

7 nights from £1098

  • Sleeps 7 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1215

4 bedroom, dog-friendly cottage with sea views near Bridport, Dorset.


Snuggled into the hillside with Golden Cap behind, The Guardhouse stands watch over this stunning part of the Jurassic Coast at Seatown, with sea views from the master bedroom and ...

  • Sleeps 7 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1215

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

7 nights from £1445

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 £1445

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

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

7 nights from £1209

5 bedroom, dog friendly self catering cottage near Bridport, Dorset.


This beautiful stone farmhouse has something very special indeed – it comes with a 450 acre wildlife and nature reserve and a unique relationship with Dorset Wildlife Trust. Quite ...

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

7 nights from £1209

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

7 nights from £2045

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 £2045

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

7 nights from £1956

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 Fri

7 nights from £1956

  • Sleeps 6 in 2 properties
  • Changeover Fri

7 nights from £1194


These two delightful properties, set deep in Dorset's beautiful countryside, are the ultimate rural retreats! To set the scene, a long, unmade farm track leads to West Farm, where ...

  • Sleeps 6 in 2 properties
  • Changeover Fri

7 nights from £1194

  • Sleeps 8 + 3 cots in 2 properties
  • Changeover Fri

7 nights from £1334


West Hembury Farm is situated in an Area of Outstanding Natural Beauty; a walker's paradise. Just four miles from the bustling market town of Bridport, and a short drive to the Wo...

  • Sleeps 8 + 3 cots in 2 properties
  • Changeover Fri

7 nights from £1334

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

7 nights from £1348


Hatts Farm is a working farm set in 100 acres on the Dorset/Wiltshire border, in an Area of Outstanding Natural Beauty near the market town of Shaftesbury and within driving distan...

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

7 nights from £1348

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