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

Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.

17 luxury self-catering cottages with outdoor pools

Treetops is a 2 bedroom, dog friendly cottage near South Molton, North Devon.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £470 *

Treetops

5815

2 bedroom, dog friendly cottage near South Molton, North Devon.


If you go down to the woods today, you'll discover a holiday abode that offers a location where you can truly recharge! Hidden in Northcote woodland in north Devon you really can e...

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

7 nights from £470 *

Darling Chestnut is a 1 bedroom self catering cottage near Helford, West Cornwall.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £625

Darling Chestnut

6009

1 bedroom self catering cottage near Helford, West Cornwall.


Resting under the ancient chestnut tree, not far from the oak-lined banks of the Helford, this beautifully converted detached barn has been curated into a dreamy retreat for two lu...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £625

View
  • 20% off

    5 Dec 2025 - 12 Dec 2025

    £781.00 £624.80

  • 20% off

    12 Dec 2025 - 19 Dec 2025

    From £781.00 £624.80

  • 20% off

    19 Dec 2025 - 26 Dec 2025

    £925.00 £740.00

  • 20% off

    26 Dec 2025 - 2 Jan 2026

    £925.00 £740.00

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 *

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 £1173 *

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 £1173 *

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 £502

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 £502

Strawberry Hole Barn is a 2 bedroom thatched, dog friendly self catering cottage near Rye.
  • Sleeps 4 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £659

Strawberry Hole Barn

5814

2 bedroom thatched, dog friendly self catering cottage near Rye.


Escape to this gorgeous thatched barn, sat in the grounds of the owners' double oast house, within walking distance of Great Dixter House and Gardens. This spacious property offers...

  • Sleeps 4 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £659

Swallows' Nest is a 2 bedroom self catering cottage near Helford, West Cornwall.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £689

Swallows' Nest

6007

2 bedroom self catering cottage near Helford, West Cornwall.


Resting in a secluded corner of rural Cornwall yet perfectly placed to explore the gentle waters of the Helford River, Swallows' Nest is a soulful and quietly luxurious barn conver...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £689

View
  • 20% off

    5 Dec 2025 - 12 Dec 2025

    £861.00 £688.80

  • 20% off

    12 Dec 2025 - 19 Dec 2025

    From £861.00 £688.80

  • 20% off

    19 Dec 2025 - 26 Dec 2025

    From £1331.00 £1064.80

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 £722

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 £722

Our guests rate us 4.8/5 on Feefo, the independent review site.

Starry Skies is a 2 bedroom self catering cottage near Helford, West Cornwall.
  • Sleeps 4 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £825

Starry Skies

6008

2 bedroom self catering cottage near Helford, West Cornwall.


Hidden away near the serene waters of the Helford River lies this thoughtfully renovated barn conversion and wild spa, where every detail has been crafted with care. From the soft-...

  • Sleeps 4 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £825

View
  • 20% off

    5 Dec 2025 - 12 Dec 2025

    £1031.00 £824.80

  • 20% off

    12 Dec 2025 - 19 Dec 2025

    From £1031.00 £824.80

  • 20% off

    26 Dec 2025 - 2 Jan 2026

    £1731.00 £1384.80

Channel View is a 4 bedroom, rural self catering cottage in Cadgwith, West Cornwall.
  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1174 *

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
  • No pets
  • Changeover Fri

7 nights from £1174 *

Load 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.