Dorset Cottages with Outdoor Swimming Pools

What better way to spend your summer holiday than in a self-catering cottage with an outdoor swimming pool? Spend your days exploring Dorset or simply relax by the pool, the choice is yours. In a Classic cottage, you can spend your holiday exactly as you please. Pour through our portfolio and find the right cottage for you. Read more

Slow dip or turbo canon-ball, whatever your style of entry entertain yourself for hours in an outdoor swimming pool. Offering properties with both shared and private pools, the whole family will have a great time paddling, swimming and floating on inflatables under the sunshine. At Classic Cottages, we have a learnt a thing or two over the years about what makes holidays great. Priding ourselves on marketing only the finest properties in Dorset, we make sure each cottage is personally inspected and fully equipped. Providing everything you could need and more, from your bed linens to your bathroom towels down to the last teaspoon, we think of everything so that you don't have to. Book with confidence with Classic Cottages. 

4 Dorset cottages with outdoor swimming pools

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

7 nights from £410 *

Gamekeeper's Cottage

4523

2 bedroom cottage with outside pool near Dorchester, Dorset.


Second in a row of pretty terraced cottages, this stylish property has been newly renovated to a very high standard. Gamekeeper's Cottage is one of four at Dominey's Yard, nestled ...

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

7 nights from £410 *

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

7 nights from £410 *

Woodcutter's Cottage

4524

2 bedroom cottage with outside pool near Dorchester, Dorset.


Rolling hills, bustling market towns, rich history and stunning beaches - have we persuaded you to holiday in Dorset yet? Finding a lovely cottage to stay in is the only thing you ...

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

7 nights from £410 *

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

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

7 nights from £410 *

Poacher's Cottage

4522

2 bedroom cottage with outside pool near Dorchester, Dorset.


Tucked away in the picturesque village of Buckland Newton, Poacher's Cottage is one of four gorgeous properties making up Dominey's Yard. Situated perfectly for exploring the beaut...

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

7 nights from £410 *

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

7 nights from £644 *

Gardener's Cottage

4525

3 bedroom cottage with outside pool near Dorchester, Dorset.


A stay at Gardener's Cottage brings you everything you could wish for in a holiday location - spacious rooms, beautiful furnishings and a stunning setting complete with outdoor hea...

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

7 nights from £644 *