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 *

British Travel Awards 2025 - Best Company For UK Holiday Home Rentals Logo

British Travel Awards 2025
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

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.

Load more
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.