Weymouth Cottages

Weymouth Cottages

A town of two halves - the old town forms a cluster of quirky mismatched cottages around the harbour, while the new town is an elegant parade of Georgian town houses on the seafront.

Our exclusive ferry discounts will make your island trip with Classic plain sailing.

We have 16 self catering cottages in Weymouth to show you...

Halcyon Cottage is a 2 bedroom cottage close to the beach, Lulworth Cove and Dorchester, Dorset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £730

Halcyon Cottage

4693

2 bedroom cottage close to the beach, Lulworth Cove and Dorchester, Dorset.


Less than two miles from Lulworth Cove, part of the only World Heritage Site in England, Halcyon Cottage is a pretty, detached stone cottage in the heart of the village of West Lul...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £730

Beehive Cottage is a 2 bedroom thatched, dog friendly cottage near Dorchester, Dorset.
  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £474

Beehive Cottage

4073

2 bedroom thatched, dog friendly cottage near Dorchester, Dorset.


Beehive Cottage is a charming and cosy cottage, on a quiet lane opposite St Mary's church in the village of Puddletown. Surrounded by farmland, the pretty village is nestled in the...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £474

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

7 nights from £627

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 £627

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

7 nights from £577

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 £577

Sturthill Stable is a 3 bedroom, dog friendly barn conversion set within a working farm near Bridport, Dorset.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £638

Sturthill Stable

2829

3 bedroom, dog friendly barn conversion set within a working farm 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 £638

Barn Owls Cottage is a 3 bedroom, dog friendly cottage near Bridport, Dorset.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £690

Barn Owls Cottage

3015

3 bedroom, dog friendly cottage near Bridport, Dorset.


Barn Owls Cottage is a semi-detached cottage that has been converted from an 18th Century stone barn. Despite having stylish modern fittings, it has still retained much of its orig...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £690

West Hembury Farm

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

7 nights from £1089

Badgers Cottage is a 1 bedroom, dog friendly cottage near Bridport, Dorset.
  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £399

Badgers Cottage

3014

1 bedroom, dog friendly cottage near Bridport, Dorset.


This pretty semi-detached cottage for two is nestled within an Area of Outstanding Natural Beauty (now known as National Landscapes) on West Hembury Farm. Badgers Cottage is an ...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £399

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

St Peter's Cottage is a 3 bedroom thatched, dog friendly cottage near Dorchester, Dorset.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £545 *

St Peter's Cottage

5135

3 bedroom thatched, dog friendly cottage near Dorchester, Dorset.


Dating back to the early 17th Century, this picture perfect, Grade II Listed thatched cottage sits in the heart of a rural Dorset village. Recently renovated by the owners, St Pete...

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

7 nights from £545 *

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

7 nights from £519

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 £519

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