Holiday Cottages with Outdoor Pools

Escape to another world when you float on the calm waters of your outdoor pool. Amongst our collection of holiday homes with outdoor swimming pools, you can wake up in luxury self-catering accommodation and head out to take a splash in your own outdoor swimming pool. Spend your days by the poolside and let your worries soak away. This is the holiday home you've been waiting for.Read more

It's not every day you can climb out of bed and lounge on a floating inflatable or have breakfast al fresco by the swimming pool. But this is your holiday so you deserve something a bit more special. Book a holiday with an outdoor pool and keep the kids entertained with no effort, or take the two of you off to float in the sunlight with no-one else around. With a selection of both shared and private swimming pools available, you can give yourself a holiday to remember. View all of our holiday cottages with a swimming pool and choose your favourite property. At Classic Cottages, we handpick all of our self-catering cottages onto our books, so you can enjoy the finest accommodation around.

17 luxury self-catering cottages with outdoor pools

  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £361

Nanteague Cottage

393

1 bedroom, dog friendly cottage with an outdoor pool Perranporth, Cornwall.


Nanteague Cottage is a spacious one bedroom cottage, ideal for couples, and with a heated swimming pool (heated by an air source heat pump and available mid-May to the mid/end of S...

  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £361

  • 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 *

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 *

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 *

  • 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 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £743 *

Channel View

3722

4 bedroom, rural self catering cottage in Cadgwith, West Cornwall.


This spectacular holiday home, located in the heart of the Lizard peninsula, is perfectly proportioned for a large family group or friends. Situated a short drive from one of t...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £743 *

  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1258 *

Orchard House

4598

4 bedroom, dog friendly holiday cottage near Okehampton, North Devon.


Perfectly situated on the edge of Dartmoor, this stunning holiday home offers fabulous outdoor space and stunning stylish interiors for all the family or a group of friends. Enjoy ...

  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1258 *

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

7 nights from £383

Orchard Dene

997

3 bedroom, dog friendly holiday cottage and a pool in Croyde


Close to some of north Devon’s best surfing beaches, Orchard Dene is in the heart of the lovely village of Georgeham, with two good pubs and a shop within walking distance. The san...

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

7 nights from £383

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

7 nights from £532

Apt 1 Springfield Court

3575

2 bedroom self catering apartment near the beach in Seaview.


Apt 1 Springfield Court is a luxurious, ground floor apartment, set in an exclusive development in the picturesque village of Seaview. It would suit a small family or a couple in n...

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

7 nights from £532

We are Gold accredited with the Green Tourism Business Scheme.

  • 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 *

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

7 nights from £781

No Place

3748

2 bedroom thatched, dog friendly cottage with sea views in Sennen.


Reputed to be the most westerly thatched cottage in Britain, No Place boasts extensive and well-maintained gardens as well as complete privacy, and is set above the white sands and...

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

7 nights from £781

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