Dorset Boltholes Available in May

Spring is well under way, the sun is shining and Dorset is looking particularly radiant. Make the most of this special time of year and treat yourself to a stay in a luxury self-catering cottage. Our collection of 23 Dorset cottages available in May have all been handpicked; personally inspected and fully equipped to ensure your stay is the best it can be.Read more

If you want to make your May half-term count this year, why not book a family holiday in Dorset? Our range of self-catering cottages come in all shapes and sizes, with plenty of room for your little ones. Many cottages have extra facilities like swimming pools, games rooms and large gardens so the kids will be in entertainment heaven while mum and dad relax. 

May isn't all about half-term though. There are two bank holidays to look forward to, and lots of opportunities to make the most of this beautiful and diverse county ahead of the summer crowds. Whether you're looking for a solo retreat, romantic couples getaway or catch up with friends, we can help you find the ideal cottage for you. If you've got a four-legged member of the family, it's great news as many of our cottages are dog-friendly too.

Dorset Cottages for May Half-Term

With its dramatic coastline, rolling countryside alive with colour and patchwork of towns and villages, Dorset provides a wonderful destination to explore, whether it's for the first time or the fifteenth. Book your Classic cottage today and be sure to receive excellent customer service with the finest quality self-catering accommodation.  

Choose from 23 available self-catering cottages in Dorset

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

7 nights from £383

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 £383

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

7 nights from £385

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 £385

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

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

7 nights from £415

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 £415

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £432

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 £432

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £536

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 £536

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

7 nights from £385

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 £385

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  • 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 £469

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 £469

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 £474

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 £474

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

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £534

2 bedroom, dog friendly holiday 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, the cot...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £534

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £568

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 £568

View
  • 15% off

    28 Jun 2019 - 5 Jul 2019

    £851.12 £723.45

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