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 10 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 10 cottages for May Day bank holiday

  • 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
  • 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

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

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £575 *

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 £575 *

  • 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

  • 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 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £569

3 bedroom self catering cottage in rural Dorset.


Meadows Barn is on the edge of the tranquil Dorset village of Halstock, with far-reaching views over the surrounding countryside, ideal for a family holiday or a great base for fri...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £569

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

7 nights from £715

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

7 nights from £715

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

7 nights from £830

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

7 nights from £830

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

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £866

3 bedroom holiday cottage in Corfe Castle, Dorset.


Situated in the popular Dorset village of Corfe Castle, on the Studland peninsula, close to the coast, this Grade II Listed picture-book cottage enjoys views of the spectacular Nat...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £866

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £885

4 bedroom holiday cottage near the beach in Studland, Dorset.


The Isle of Purbeck is a stunning Area of Outstanding Natural Beauty between Poole and Swanage boasting one of the most spectacular coastlines in Dorset. Sunnyholme, an extremel...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £885