Dorset Boltholes with Enclosed Gardens

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

17 retreats with enclosed gardens in Dorset

The Dairy is a 1 bedroom cottage near the Jurassic Coast near Bridport, Dorset.
  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £363

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
  • No pets
  • Changeover Sat

7 nights from £363

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

7 nights from £376

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 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 £376

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

7 nights from £492 *

Crosskeys Cottage

4855

3 bedroom, dog friendly holiday cottage near Beaminster, Dorset.


Situated in the pretty west Dorset village of Broadwindsor, surrounded by countryside and not far from the coast, Crosskeys Cottage is a wonderful place to spend your holiday. Buil...

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

7 nights from £492 *

The Old Coach House is a 2 bedroom, dog friendly cottage near the county town of Dorchester, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £463

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 £463

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

7 nights from £490

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, the cot...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £490

Celtic Blessing is a 2 bedroom cottage near Bridport, Dorset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £512

Celtic Blessing

2256

2 bedroom 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
  • No pets
  • Changeover Fri

7 nights from £512

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  • 20% off

    21 Dec 2023 - 28 Dec 2023

    £869.00 £695.20

  • 10% off

    28 Dec 2023 - 2 Jan 2024

    £695.20 £625.68

The Old Dairy is a 2 bedroom, dog friendly former milking parlour near Blandford Forum, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £517

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 £517

Pebbles is a 2 bedroom, dog friendly cottage near the beach in West Bay, Dorset.
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £542

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 £542

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Meadowbank is a 3 bedroom house with countryside views near Bridport, Dorset.
  • Sleeps 5 + cot
  • No pets
  • Changeover Sat

7 nights from £495

Meadowbank

2644

3 bedroom house with countryside views near Bridport, Dorset.


This sunny south-facing cottage is sat perfectly on the edge of the beautiful village of Netherbury. If you are looking for a peaceful, rural setting to spend your well deserved ho...

  • Sleeps 5 + cot
  • No pets
  • Changeover Sat

7 nights from £495

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

7 nights from £650

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 £650

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