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 16 cottages in Dorset for May half term

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

7 nights from £465

1 bedroom, rural holiday cottage near Dorchester, Dorset.


Dorset’s World Heritage Jurassic Coast is close to this comfortably furnished, single-storey, spacious cottage. Set within the grounds of the Owner’s home, The Stables is self-cont...

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

7 nights from £465

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

7 nights from £481

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


This cosy, compact, delightful bolthole for two is set in a wonderfully tranquil hamlet in north Dorset with village shops and a choice of two pubs within two miles. Built in lo...

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

7 nights from £481

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

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

7 nights from £485

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


The Dairy is another extremely comfortable single-storey cottage in this small and friendly farm development. This property has French windows to its own enclosed outside space – t...

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

7 nights from £485

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £674

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 £674

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £485

1 bedroom, dog friendly 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 3 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £485

View
  • 15% off

    29 Jun 2019 - 6 Jul 2019

    £522.35 £444.00

  • 10% off

    13 Jul 2019 - 20 Jul 2019

    £565.88 £509.29

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £636

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 £636

View
  • 15% off

    28 Jun 2019 - 5 Jul 2019

    £646.91 £549.87

  • 10% off

    12 Jul 2019 - 19 Jul 2019

    £724.85 £652.37

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £643

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 £643

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

7 nights from £961

2 bedroom, rural holiday cottage near Bridport, Dorset.


Nestling in a picturesque valley a fifteen minute drive from the Jurassic Coast, Barbridge Cottage is close to beaches, walks, fossil hunting, country houses, gardens and lovely pu...

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

7 nights from £961

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

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

7 nights from £829

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


The Parlour is an excellent choice for a family, with French windows opening out onto an enclosed gravelled patio, comfortable accommodation for five guests – one of the three sing...

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

7 nights from £829

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

7 nights from £1073

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 £1073

View
  • 15% off

    28 Jun 2019 - 5 Jul 2019

    £1063.90 £904.31

  • 10% off

    12 Jul 2019 - 19 Jul 2019

    £1197.72 £1077.95

Loading more