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 26 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 26 available self-catering cottages in Dorset

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

7 nights from £371

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
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £371

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

7 nights from £376

1 bedroom thatched self catering cottage near Sherborne, Dorset.


Pound Farm Cottage is a hidden gem; this listed thatched cottage has been thoughtfully renovated to create a spacious, stylish holiday home, retaining many of the original features...

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

7 nights from £376

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  • 15% off

    22 Apr 2019 - 26 Apr 2019

    £342.75 £291.34

  • 15% off

    3 May 2019 - 10 May 2019

    £442.50 £375.70

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

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £423

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 £423

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £550 *

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 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £550 *

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £401

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 £401

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

7 nights from £444

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 £444

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

7 nights from £469

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 £469

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £500

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 £500

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

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £503

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 £503

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

7 nights from £512

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 £512

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