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 16 available retreats with enclosed gardens and find your perfect one. The holiday of a lifetime is but moments away. 

16 retreats with enclosed gardens in Dorset

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

7 nights from £332

The Dairy

2663

1 bedroom cottage near the Jurassic Coast 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.


This pretty semi-detached cottage for two is nestled within an Area of Outstanding Natural Beauty on West Hembury Farm. Badgers Cottage is an 18th Century stone barn that has be...

  • 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, rural dog friendly 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 cottage near the county town of Dorchester, Dorset.


This pretty detached former coach house can be found in the rural Dorset countryside, within easy reach of the stunning coastlines of the Jurassic Coast, a World Heritage Site. ...

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

7 nights from £473

The Old Dairy

4740

2 bedroom, dog friendly former milking parlour near Blandford Forum, Dorset.


This former milking parlour that served the local farm has been beautifully converted into a fabulous holiday home. Situated in a picturesque Dorset village that is full of charact...

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

7 nights from £473

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

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

7 nights from £506

Pebbles

4681

2 bedroom, dog friendly cottage near the beach in West Bay, Dorset.


Situated a short stroll from the dramatic beauty of the Jurassic coastline and the charming harbour at West Bay, Pebbles is a fabulous base for your Dorset holiday. Close to the se...

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

7 nights from £506

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

7 nights from £436

Meadowbank

2644

3 bedroom house with countryside views near Bridport, Dorset.


If you are looking for a peaceful, rural setting to spend your well deserved holiday, then look no further. This sunny south-facing cottage is sat perfectly on the edge of the beau...

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

7 nights from £436

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