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.
20 luxury self-catering cottages with outdoor pools
7 nights from £403
Nanteague Cottage
3931 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 (shared with the owners and heated by an air source heat pump and available ...
7 nights from £403
7 nights from £453
Gamekeeper's Cottage
45232 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 ...
7 nights from £453
Our property managers are local experts who handpick perfect places to stay.
Local experts
We scour the coast and country to winkle out bits worth sharing with you, the best properties in lovely locations. While we’re out and about, we gather together the best things to do so that you can start planning your holiday as soon as you’ve booked.
The ‘Explore Nearby’ tab on our cottage pages show what’s nearby along with relevant articles from our holiday guides from Notes and Stories, where you’ll find hand-written experiences of outings across the South and West, from dog-friendly pubs on the Isle of Wight to free things to do in south Devon and everything in between.
7 nights from £453
Woodcutter's Cottage
45242 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 ...
7 nights from £453
7 nights from £453
Poacher's Cottage
45222 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...
7 nights from £453
7 nights from £659 *
Gardener's Cottage
45253 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...
7 nights from £659 *
7 nights from £861 *
Rydon
55053 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...
7 nights from £861 *
7 nights from £906 *
Sunset Cottage
43193 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...
7 nights from £906 *
7 nights from £1294 *
Marnylunn
47174 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...
7 nights from £1294 *
We are Gold accredited with the Green Tourism Business Scheme.
Green Tourism Business Scheme
As a company, we look across our business and try to make sustainable changes and decisions. From using recycled paper in our printers to putting in measures for using less energy in our offices, we keep an eye on our impact on the environment.
Beyond our offices, we have passed on the same ethics to our holiday cottage owners by setting up our own Green Scheme that they can join. Each property has to tick off a certain number of actions to be included in the scheme, many of which go above and beyond the GTBS requirements.
7 nights from £486
Orchard Dene
9973 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...
7 nights from £486
7 nights from £701
Apt 1 Springfield Court
35752 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...
7 nights from £701