Cottages near Pilsdon Pen

Cottages near Pilsdon Pen

We've got 11 holiday cottages within 5 miles of Pilsdon Pen. You can refine your search using the controls below.

Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.

We have 11 self catering cottages near Pilsdon Pen to show you...

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 £378

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 £378

View
  • 40% off

    19 Jun 2026 - 26 Jun 2026

    £840.00 £504.00

  • 40% off

    26 Jun 2026 - 3 Jul 2026

    £840.00 £504.00

Swallows' Rest is a 1 bedroom, dog friendly cottage near Beaminster, Dorset.
  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £412

Swallows' Rest

4644

1 bedroom, dog friendly cottage near Beaminster, Dorset.


The sleepy west Dorset countryside awaits you at this cute bolthole for two (plus your four-legged friends). Tucked away at the end of the owners' garden, this converted barn is hi...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £412

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

7 nights from £431 *

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 £431 *

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

7 nights from £431 *

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 £431 *

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Best company for UK holiday home rentals

Whetley Farm

  • Sleeps 8 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £861

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 £412

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 £412

Hood's is a 2 bedroom, dog friendly self catering cottage near Bridport, Dorset.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1050

Hood's

6045

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


**Hood's can accommodate flexible check in days – please contact us to request.** This stunning barn and milking parlour conversion is set within the glorious Dorset countryside...

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

7 nights from £1050

View
  • 20% off

    19 Jun 2026 - 26 Jun 2026

    £1750.00 £1400.00

  • 20% off

    26 Jun 2026 - 3 Jul 2026

    £1750.00 £1400.00

Hood's and Loaf at Kingsland Farm

  • Sleeps 6 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £1462

Bay Tree Cottage is a 3 bedroom, dog friendly cottage near Bridport, Dorset.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £556 *

Bay Tree Cottage

4835

3 bedroom, dog friendly cottage near Bridport, Dorset.


Situated in a sleepy west Dorset village, just a short drive from the spectacular Jurassic Coast, you will find this pretty terraced cottage. Bay Tree Cottage offers all the deligh...

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

7 nights from £556 *

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 £78 per night

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 £78 per night

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Traditionally thought of as Dorset's highest peak (277m), until it was recently found to be a few feet shy of its neighbour, Lewesdon Hill. Height notwithstanding, the Iron Age hill fort atop this flat-topped hill provides great views over the lush Marshwood Vale in west Dorset. Walk the ancient ramparts in a circular loop to take in the 360 degree panorama across the gentle rolling hills, whilst buzzards wheel overhead. Reach it off the B3164 Broadwindsor road.