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 36 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 36 available self-catering cottages in Dorset

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

7 nights from £371

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  • 20% off

    29 Dec 2018 - 5 Jan 2019

    £522.00 £417.60

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

7 nights from £371

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 £371

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  • 20% off

    22 Dec 2018 - 29 Dec 2018

    £522.00 £417.60

  • 20% off

    29 Dec 2018 - 5 Jan 2019

    £522.00 £417.60

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

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

7 nights from £375

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


This cosy, compact yet 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...

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

7 nights from £375

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £381

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 £381

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

7 nights from £387

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 £387

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  • 20% off

    21 Dec 2018 - 28 Dec 2018

    £578.65 £463.20

  • 20% off

    28 Dec 2018 - 4 Jan 2019

    £578.65 £463.20

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

7 nights from £420

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 £420

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  • 25% off

    17 Dec 2018 - 23 Dec 2018

    £635.00 £476.25

  • 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 2
  • Regret no pets
  • Changeover Fri

7 nights from £525

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 £525

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

  • 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
  • Dogs welcome
  • Changeover Fri

7 nights from £436

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 £436

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  • 40% off

    21 Dec 2018 - 28 Dec 2018

    £651.55 £391.20

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