Dorset Boltholes with Enclosed Gardens

In a self-catering cottage with an enclosed garden you and your family can enjoy some added privacy and security. Help contain lively legs and take a look at our luxury portfolio in Dorset. At Classic Cottages, we want your whole experience to be the best it can be and handpick all of our cottages onto our books. Find your cottage today for dreams tomorrow. Read more

Whether you are looking for family-friendly accommodation or a dog-friendly cottage with an enclosed garden, we have a selection of properties available in Dorset for you to choose from. To give you some added reassurance, let your kids play and your dog sniff around in a garden offering more security. You'll be able to relax knowing your loved ones are nearby.

Cottages with Enclosed Gardens in Dorset 

Across Dorset we have a range of beautiful self-catering cottages of all shapes and sizes. Priding ourselves on marketing only the finest self-catering accommodation around, we want your holiday in Dorset to be the best it can be. Browse our selection of 14 available retreats with enclosed gardens and find your perfect one. The holiday of a lifetime is but moments away. 

14 retreats with enclosed gardens in Dorset

New bookings can be placed for any holiday arriving on or after the 12th April for cottages in England and we are accepting Easter bookings at our properties in Wales, for those that can legally travel. COVID-19

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £332

The Dairy

2663

1 bedroom, rural cottage near the beach 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
  • Regret no pets
  • Changeover Sat

7 nights from £332

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £345

Badgers Cottage

3014

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


Badgers Cottage, a snug semi-detached cottage for two, is set in a farmyard, beautifully converted from an 18th Century stone barn. All on one level, the open plan design gives a w...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £345

Need more time? Reserve any cottage for up to 24 hours before booking.

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £414

Cedar Lodge

4014

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


Cedar Lodge is a cosy cottage in a quiet rural location. All on one level, the open plan living-room with kitchen and dining areas create a very sociable space for a couple or smal...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £414

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £415

Celtic Blessing

2256

2 bedroom holiday cottage near Bridport, Dorset.


Close to Dorset's spectacular Jurassic Coast, the popular market town of Bridport and the harbour and beach at West Bay, this cottage has stunning views of the gentle Dorset countr...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £415

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

7 nights from £424

The Old Coach House

1386

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


This pretty, detached former coach house is in beautiful rural Dorset, and within easy reach of the stunning World Heritage Jurassic coastline. The Old Coach House has a spaciou...

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

7 nights from £424

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £449

Ivy Cottage

4122

2 bedroom, dog friendly holiday 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, the cot...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £449

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £463

September Cottage

2948

2 bedroom self catering cottage near the sea near Weymouth, Dorset.


This comfortable semi-detached family home is on the edge of the countryside, yet only three miles from Weymouth with its sandy beaches and historic quay. A 20 minute walk takes yo...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £463

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £436

Meadowbank

2644

3 bedroom holiday cottage near Bridport, Dorset.


This sunny south-facing cottage enjoys a quiet rural position on the edge of the beautiful village of Netherbury, a short drive from the beaches and cliffs of the World Heritage Ju...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £436

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £595

Barn Owls Cottage

3015

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


Barn Owls Cottage, a semi-detached cottage converted from an 18th Century stone barn, has retained much of its original character with inset fossils and huge oak beams. The kitchen...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £595

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £643

2 Penny’s Cottages

2531

3 bedroom holiday cottage in Corfe Castle, Dorset.


You will be completely spoilt for choice in this stunning part of Dorset – along the Jurassic Coast and within very easy reach are Lulworth Cove and Durdle Door with their famous c...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £643

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