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. 

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

25 retreats with enclosed gardens in Dorset

4 bedroom holiday cottage near the beach in Studland, Dorset.


The Isle of Purbeck is a stunning Area of Outstanding Natural Beauty between Poole and Swanage boasting one of the most spectacular coastlines in Dorset. Sunnyholme, an extremel...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

Price per week £646 - £1806

3 bedroom, dog friendly cottage near the beach in Christchurch.


Avon Beach, Christchurch Harbour, the New Forest National Park and the Jurassic Coast are all nearby to this recently renovated holiday bolthole. The cool shades of blue and the pl...

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

Price per week £725 - £1495

5 bedroom, dog friendly cottage near the beach near Lyme Regis.


Less than half a mile from the World Heritage Jurassic Coast, The Old Manor House is a beautiful 16th Century, Grade II Listed house, full of character with a delightful enclosed g...

  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

Price per week £1043 - £3260 *

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* Includes 20% off for parties up to 6 + 2 cots on selected dates. Bedrooms 3 and 5 are excluded at the discounted rate.

  • 10% off

    2 Nov 2018 - 9 Nov 2018

    £1073.86 £966.47


West Hembury Farm is situated in an Area of Outstanding Natural Beauty; a walker's paradise. Just four miles from the bustling market town of Bridport, and a short drive to the Wo...

  • Sleeps 8 + 3 cots in 2 properties
  • Changeover Fri

Price per week £826 - £2002


Nestled into the hillside overlooking rolling green Dorset countryside, these three gorgeous lodges provide a holiday location where you can simply unwind from the moment you arriv...

  • Sleeps 13 + 3 cots in 3 properties
  • Changeover Fri

Price per week £1374 - £2988