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.

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 27 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 27 cottages for May Day bank holiday

2 bedroom holiday cottage near Bridport, Dorset.


Close to Dorset's spectacular Jurassic Coast, the popular market town of Bridport and the harbour and beach at West Bay, this cottage has stunning views of the gentle Dorset countr...

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

Price per week £478

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

Price per week £519

2 bedroom, dog friendly holiday cottage 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

Price per week £523

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

Price per week £557

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

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

Price per week £696

3 bedroom, dog friendly self catering cottage near Bridport, Dorset.


Barn Owls Cottage, a semi-detached cottage converted from an 18th Century stone barn, has retained much of its original character with inset fossils and huge oak beams. The kitchen...

  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

Price per week £711

3 bedroom, dog friendly self catering cottage near Bridport, Dorset.


This beautiful barn conversion at the heart of a working dairy farm is just inland from Dorset's spectacular Jurassic Coast and its beaches. The rural setting will please all the f...

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

Price per week £715

3 bedroom thatched, dog friendly cottage in Tolpuddle, Dorset.


This very pretty thatched cottage is in the tranquil historic village of Tolpuddle, surrounded by beautiful countryside and just 15 miles from the World Heritage Jurassic Coast. Wi...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £719

3 bedroom, dog friendly holiday cottage near Lyme Regis, Dorset.


Imagine spending a week in a fabulous former dairyman’s cottage with all mod-cons! This very stylishly furnished, yet quirky, semi-detached cottage is in the village of Morcombelak...

  • Sleeps 6
  • Dogs welcome
  • Changeover Fri

Price per week £772

3 bedroom holiday cottage in Corfe Castle, Dorset.


You will be completely spoilt for choice in this stunning part of Dorset – along the Jurassic Coast and within very easy reach are Lulworth Cove and Durdle Door with their famous c...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

Price per week £830

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

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