Cottages in Dorset for May Day Bank Holiday

Pick from 39 cottages for May Day bank holiday

Primrose Cottage is a 2 bedroom, dog friendly self catering cottage in Bridport, Dorset.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £589 * booking fees included

Primrose Cottage

6179

2 bedroom, dog friendly self catering cottage in Bridport, Dorset.


Primrose Cottage is the quintessential Dorset coastal property with its pretty village location and gorgeous, enclosed garden - it is packed with character. This semi-detached two ...

  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £589 *

Minnie's Cottage is a 2 bedroom, dog friendly cottage near the beach near Bridport.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £589 * booking fees included

Minnie's Cottage

6126

2 bedroom, dog friendly cottage near the beach near Bridport.


Minnie's Cottage is a cosy quintessential thatched cottage in the beautiful coastal village of Burton Bradstock. Situated in the heart of the village and just half a mile from the ...

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

7 nights from £589 *

Tolpuddle Cottage is a 3 bedroom thatched, dog friendly cottage in Tolpuddle, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £605 * booking fees included

Tolpuddle Cottage

3752

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 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £605 *

Toby's Hut is a Luxury dog friendly shepherds hut with a hot tub near Lyme Regis, Dorset.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

From £81 per night + £53 booking fees

Toby's Hut

4723

Luxury dog friendly shepherds hut with a hot tub near Lyme Regis, Dorset.


Located in the west Dorset Area of Outstanding Natural Beauty and just a 15 minute drive from fabulous Lyme Regis, Toby's Hut is a bespoke Shepherd's Hut, sitting in a perfect spot...

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

From £81 per night

Loaf At The Granary is a 1 bedroom, dog friendly self catering cottage near Bridport, Dorset.
  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

7 nights from £641 booking fees included

Loaf At The Granary

6046

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


**Loaf At The Granary can accommodate flexible check in days – please contact us to request.** Loaf At The Granary is a gorgeous and sympathetic restoration of an ancient Dorset...

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

7 nights from £641

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

7 nights from £665 * booking fees included

The Old Dairy

5551

2 bedroom, dog friendly cottage near Wimborne Minster, Dorset.


The Old Dairy is one of the most stunning holidays homes you could visit with curated interior touches at every turn. It’s location for local exploring is particularly good with so...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £665 *

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

Lavender Cottage is a 2 bedroom, dog friendly cottage near the beach in Christchurch.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £701 * booking fees included

Lavender Cottage

6176

2 bedroom, dog friendly cottage near the beach in Christchurch.


Lavender Cottage is a delightful two bedroom home with open plan living areas and wonderful outdoor space. Set in the exclusive Wick Village it is just a short walk from one of Dor...

  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £701 *

Seymour Barn is a 2 bedroom, dog friendly barn conversion in Bridport, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £742 * booking fees included

Seymour Barn

5314

2 bedroom, dog friendly barn conversion in Bridport, Dorset.


With the bustling market town of Bridport within striking distance, this beautiful barn conversion is the perfect home-away-from-home. A delightful spot to explore all the beauty a...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £742 *

The Old School Gables is a 2 bedroom cottage near the market town of Bridport, Dorset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £441 booking fees included

The Old School Gables

2490

2 bedroom cottage near the market town of 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 extrem...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £441

View
  • 40% off

    24 Jul 2026 - 31 Jul 2026

    £693.00 £441.00 booking fees included

  • 40% off

    31 Jul 2026 - 7 Aug 2026

    £693.00 £441.00 booking fees included

Freshfields is a 4 bedroom self catering cottage near Dorchester, Dorset.
  • Sleeps 7 + cot
  • No pets
  • Changeover Fri

7 nights from £640 * booking fees included

Freshfields

5706

4 bedroom self catering cottage near Dorchester, Dorset.


Freshfields is a truly outstanding property in a picturesque Dorset village. Recently renovated throughout, the house provides space and privacy for all the family. Just a short dr...

  • Sleeps 7 + cot
  • No pets
  • Changeover Fri

7 nights from £640 *

View
  • 25% off

    31 Jul 2026 - 7 Aug 2026

    £2265.00 £1714.50 booking fees included

  • 25% off

    14 Aug 2026 - 21 Aug 2026

    From £2265.00 £1714.50 booking fees included

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