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

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 windows to its own enclosed outside space – t...

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

Price per week £307 - £592

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

Price per week £315 - £607

Don’t miss out; reserve your favourite 2019 holiday cottage for just £30

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 creates a very sociable space for a couple or sma...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £389 - £795

2 bedroom, rural holiday cottage near Dorchester, Dorset.


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

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

Price per week £399 - £1018

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

Price per week £401 - £827

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  • 10% off

    29 Sep 2018 - 5 Oct 2018

    £415.80 £374.22

  • 10% off

    12 Oct 2018 - 19 Oct 2018

    £461.70 £415.80

2 bedroom, rural self catering cottage near Beaminster, Dorset.


A stunning west Dorset location, amazing rural views and a truly luxurious property, Phoebes House is a hidden gem just a short drive inland from the famous Jurassic Coast. This de...

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

Price per week £428 - £1092

2 bedroom, dog friendly holiday cottage 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

Price per week £431 - £936

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

Price per week £444 - £897

We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.

2 bedroom, rural self catering cottage near Beaminster, Dorset.


With stunning rural views from your deck, and a fabulous open plan interior, Furrow Lodge snuggles into the hillside in the delightful Dorset countryside and offers a real opportun...

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

Price per week £449 - £975

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


Lynchet Lodge is a gorgeous open plan cottage, beautifully furnished and equipped to provide all that you need for a relaxing holiday in rural Dorset. The open plan kitchen/dining/...

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

Price per week £449 - £975

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