Holiday Cottages with Outdoor Pools

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.

19 luxury self-catering cottages with outdoor pools

Nanteague Cottage is a 1 bedroom, dog friendly cottage with an outdoor pool Perranporth, Cornwall.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £403

Nanteague Cottage

393

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


A spacious cottage, in pretty countryside and with a heated swimming pool - what a find. Located on Nanteague Farm which spreads over 130 acres with a beautifully landscaped coarse...

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

7 nights from £403

Woodcutter's Cottage is a 2 bedroom cottage with outside pool near Dorchester, Dorset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £453

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
  • No pets
  • Changeover Fri

7 nights from £453

Poacher's Cottage is a 2 bedroom cottage with outside pool near Dorchester, Dorset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £453

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
  • No pets
  • Changeover Fri

7 nights from £453

Gardener's Cottage is a 3 bedroom cottage with outside pool near Dorchester, Dorset.
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £659 *

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
  • No pets
  • Changeover Fri

7 nights from £659 *

Rydon is a 3 bedroom, dog friendly cottage near Bovey Tracey, South Devon.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £861 *

Rydon

5505

3 bedroom, dog friendly cottage near Bovey Tracey, South Devon.


Introducing Rydon, a 15th Century barn which has been restored and crafted into this most luxurious and comfortable retreat. This 'once upon a time' flower store has been architect...

  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £861 *

Sunset Cottage is a 3 bedroom self catering cottage near Ventnor, Isle of Wight
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £906 *

Sunset Cottage

4319

3 bedroom self catering cottage near Ventnor, Isle of Wight


Looking for the ultimate homestay for a family holiday, a celebratory escape for a couple, or simply an excuse to get together with friends, Sunset Cottage has holiday luxury cover...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £906 *

Marnylunn is a 4 bedroom, dog friendly cottage with sea views near Helford.
  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sun

7 nights from £1294 *

Marnylunn

4717

4 bedroom, dog friendly cottage with sea views near Helford.


A luxurious residence with far reaching sea views offering a real home-from-home any time of year, and in the idyllic and tranquil setting of Gillan Creek, Marnylunn means 'mariner...

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sun

7 nights from £1294 *

Orchard Dene is a 3 bedroom, dog friendly holiday cottage and a pool in Croyde
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £486

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 £486

We’re here to help you find your perfect place to stay 7 days a week.

Apt 1 Springfield Court is a 2 bedroom self catering apartment near the beach in Seaview.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £701

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
  • No pets
  • Changeover Fri

7 nights from £701

3 Springfield Court is a 3 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £725

3 Springfield Court

3547

3 bedroom self catering apartment near the beach in Seaview, Isle of Wight.


With a comfortable interior, an unbeatable location, manicured grounds and the beach within easy reach, 3 Springfield Court has it all. This delightful holiday home would suit a fa...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £725

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