Dorset Cottages Available for May Half Term

Dorset Cottages Available for May Half Term

With temperatures warming, long daylight hours and a dazzling sun in the sky, it can mean only one thing: summer is coming. Make the most of your May half term and head to Dorset to luxuriate in your own private self-catering cottage. Gather your troops, pack your bags and hop in the car; the holiday of a lifetime is ready and waiting. Read more

If you've got children in tow, why not book yourselves into a luxury self-catering cottage this May half term? From babies to young children to teenagers, our portfolio includes properties of a wide variety and consistent quality. Pick a cottage with a private swimming pool, or find one with a games room; kids will find plenty to entertain themselves with whilst mum and dad sit back and relax.

However you want to plan your dream retreat, we'll help you to find your perfect place. From one-bed cottages for solo retreats to big family-friendly home-from-homes, let your imagination soar as you pour through our selection of available cottages in Dorset.

Cottages for May Half Term in Dorset

At Classic Cottages we pride ourselves on marketing only the finest quality self-catering cottages in Dorset. All of our cottages are personally inspected to meet exacting standards; carefully selected and fully equipped so that you can spend the holiday of a lifetime without worrying about a thing. 

Stay in one of our 21 cottages in Dorset for May half term

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

7 nights from £918

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 £918

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

7 nights from £611

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 £611

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

7 nights from £989

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 £989

Periwinkle Cottage is a 1 bedroom, dog friendly self catering cottage in Bridport, Dorset.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £482

Periwinkle Cottage

5258

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


Tucked away off one of Bridport's vibrant streets is Periwinkle Cottage, a beautiful home ready to welcome you for a fantastic stay. This gorgeous terraced retreat is the perfect p...

  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £482

Ginny's Barn is a 2 bedroom, self catering cottage near Bridport, Dorset.
  • Sleeps 3
  • No pets
  • Changeover Fri

7 nights from £636

Ginny's Barn

5276

2 bedroom, self catering cottage near Bridport, Dorset.


Find your 'Far from the Madding Crowd' moment in the beautiful west Dorset countryside with a stay at Ginny's Barn. This quaint cottage is set in the grounds of the owners' home an...

  • Sleeps 3
  • No pets
  • Changeover Fri

7 nights from £636

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 £1015

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 £1015

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 £705 *

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 £705 *

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 £760

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 £760

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

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 £703

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 £703

Fox Cottage is a 1 bedroom stylish cottage in Beaminster, Dorset.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £678

Fox Cottage

4712

1 bedroom stylish cottage in Beaminster, Dorset.


Tucked away in an oh-so-pretty part of historic Beaminster, Fox Cottage is a gorgeous retreat for two. As soon as you arrive at this picture-perfect terraced cottage, you will want...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £678

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