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.
18 luxury self-catering cottages with outdoor pools
7 nights from £361
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 £361
7 nights from £410 *
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 £410 *
Need more time? Reserve any cottage for up to 24 hours before booking.
24hr no commitment reservations
You can reserve your holiday dates on your favourite cottage for up to 24 hours. You might need to check with other guests in your party or simply consider whether this cottage is right for your holiday, either way we’re happy to give you the time to step away and mull over your options before paying a penny.
We’ll send you a reminder to see if you want it or not so you won’t lose out. Take time to think it over, you don’t have to rush your decision. Have a cup of tea and when you’re ready, hit the button to book your holiday and start looking forward to it.
7 nights from £410 *
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 £410 *
7 nights from £410 *
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 £410 *
7 nights from £743 *
Channel View
37224 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...
7 nights from £743 *
7 nights from £1134 *
Orchard House
45984 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 ...
7 nights from £1134 *
7 nights from £383
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 £383
7 nights from £532
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 £532
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 £644 *
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 £644 *
7 nights from £781
No Place
37482 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...
7 nights from £781