Cottages in Dorset for May Day Bank Holiday

Escape from the rhythm of everyday life and kick start your summer. Across Dorset, colours and new life pervade the landscape and lots of events and festivities take place. Choose a luxury cottage from which to enjoy Dorset this May Day bank holiday and spend your break in a home-from-home. All of our cottages have been personally inspected and handpicked.Read more

Planning on a solo escape this May Day to relax and revive? How about a romantic retreat in a cosy cottage for two? Perhaps you'd like to enjoy a family break and spend some quality time together in a spacious retreat? From country to coast, we have a range of luxury self-catering cottages in Dorset, primed and ready to welcome you. Many are dog-friendly too, so no one gets left behind. Choose from our 15 available properties and get ready to spend a May Day bank holiday to remember. At Classic Cottages, we understand what makes holidays fantastic and pride ourselves on marketing the finest self-catering accommodation around. With each holiday cottage regularly inspected and fully equipped, everything you could need and more for your stay is supplied. Book with confidence with Classic Cottages. 

Pick from 15 cottages for May Day bank holiday

  • 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

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

7 nights from £405

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 £405

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  • 15% off

    29 Mar 2019 - 5 Apr 2019

    £377.00 £320.45

  • 15% off

    5 Apr 2019 - 12 Apr 2019

    £431.38 £366.35

  • 15% off

    12 Apr 2019 - 19 Apr 2019

    £431.38 £366.35

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 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £443

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 £443

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  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £405.45 £324.36

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £419

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 £419

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  • 10% off

    22 Mar 2019 - 29 Mar 2019

    £390.00 £351.00

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

7 nights from £480

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 £480

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  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £434.62 £347.70

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

7 nights from £540

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 £540

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

7 nights from £490

3 bedroom holiday cottage near Bridport, Dorset.


This sunny south-facing cottage enjoys a quiet rural position on the edge of the beautiful village of Netherbury, a short drive from the beaches and cliffs of the World Heritage Ju...

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

7 nights from £490

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

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

7 nights from £621

2 bedroom, rural holiday cottage near Shaftesbury, Dorset.


Semi-detached Hatts Barn is a contemporary, reversed level barn conversion on a wide south-facing terrace. The large en suite master bedroom and a twin bedded family room (the beds...

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

7 nights from £621

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  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £536.36 £429.09

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

7 nights from £696

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 £696

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  • 20% off

    22 Mar 2019 - 29 Mar 2019

    £600.60 £480.48

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