Cottages in Dorset for May Day Bank Holiday

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 26 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 26 cottages for May Day bank holiday

The Linhay is a 1 bedroom cottage near the beach near Bridport, Dorset.
  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £377

The Linhay

2661

1 bedroom cottage near the beach near Bridport, Dorset.


The Linhay is a tucked away single-storey retreat – and an ideal base for exploring the wonderful coastline. The cottage nestles alongside the barns, with a fully enclosed gravel c...

  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £377

The Dairy is a 1 bedroom cottage close to the Jurassic Coast, near Bridport, Dorset.
  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £400

The Dairy

2663

1 bedroom cottage close to the Jurassic Coast, near Bridport, Dorset.


The Dairy is another extremely comfortable single-storey cottage in this small and friendly farm development. This property has French doors to its own enclosed outside space – the...

  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £400

The Granary is a 2 bedroom, dog friendly holiday cottage near Beaminster, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £458

The Granary

5683

2 bedroom, dog friendly holiday cottage near Beaminster, Dorset.


Tucked away in a rural corner of west Dorset you will find The Granary; a single-storey cottage with a shared two acre woodland and wildflower meadow to while away holiday days in....

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £458

The Dairy is a 2 bedroom, dog friendly holiday cottage near Beaminster, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £458

The Dairy

5682

2 bedroom, dog friendly holiday cottage near Beaminster, Dorset.


A cosy single-storey cottage, a secret wood and wildflower meadow, all available to you in a location only a short drive of the World Heritage Jurassic Coast, are we tempting you y...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £458

Old Sandpitts Cottage is a 2 bedroom thatched cottage near Bridport, Dorset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £477

Old Sandpitts Cottage

4504

2 bedroom thatched cottage near Bridport, Dorset.


Tucked away down its own private track, this picture-perfect thatched cottage is a little gem. Surrounded by its own private garden, the cottage is very peaceful and offers space f...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £477

The Gardens is a 2 bedroom, dog friendly cottage in historic Sherborne, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £503

The Gardens

5406

2 bedroom, dog friendly cottage in historic Sherborne, Dorset.


From the rolling hills of the Dorset countryside to the beautiful historic streets of Sherborne and down to the Jurassic Coast, explore it all whilst staying at The Gardens. This c...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £503

The Old Coach House is a 2 bedroom, dog friendly cottage near the county town of Dorchester, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £506

The Old Coach House

1386

2 bedroom, dog friendly cottage near the county town of Dorchester, Dorset.


This pretty detached former coach house can be found in the rural Dorset countryside, within easy reach of the stunning coastlines of the Jurassic Coast, a World Heritage Site. ...

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

7 nights from £506

Pippins is a 3 bedroom, dog friendly character cottage near Beaminster, Somerset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £507

Pippins

5360

3 bedroom, dog friendly character cottage near Beaminster, Somerset.


Pippins is a picture postcard country cottage nestled in the charming Somerset village of North Perrott - not far from the Dorset border. This cosy home can cater for all of the fa...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £507

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

Ivy Cottage is a 2 bedroom, dog friendly cottage in Cattistock near Dorchester, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £529

Ivy Cottage

4122

2 bedroom, dog friendly 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 (now ren...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £529

Rectory Cottage is a 2 bedroom cottage near Bridport, Dorset
  • Sleeps 4 + cot
  • No pets
  • Changeover Mon

7 nights from £639

Rectory Cottage

4795

2 bedroom cottage near Bridport, Dorset


Hidden away in the grounds of a Grade II Listed former rectory, this picture-perfect cottage is a delightful Dorset escape. From the moment you pull into the driveway you will love...

  • Sleeps 4 + cot
  • No pets
  • Changeover Mon

7 nights from £639

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